Chem and Orgo Flashcards

Question

How does decreasing salt concentration affect hydrophobic chromatography?

Answer 1

Hydrophobic chromatography relies on high salt concentrations to strengthen hydrophobic interactions Decrease causes protein to dissociate from column

Answer 2

390-700nm Violet- 390nm Red- 700nm

Answer 3

Trans has higher BP cis generally more compact, trans generally linear—> pack tighter

Answer 4

Glucose (6 membered) + fructose (5 membered)

Answer 5

Deoxyribose = no 3’ hydroxyl So Dideoxyribose = no 2’ or 3’ hydroxyl

Answer 6

E = hf0 where E is the work function, h is Planck’s constant, f0 is threshold frequency Minimum energy needed to remove valence electrons

Answer 7

Excess energy is transferred to kinetic energy of ejected electron

Answer 8

The work function = the energy So the electron will be free from its attraction to the nucleus But it will not move because it lacks excess energy to be converted to KE

Answer 9

Alpha decay- loss of one He nucleus, which has mass number of 4 and atomic number of 2

Answer 10

Beta decay- neutron chantes to proton, electron ejected

Answer 11

Gamma emission- byproduct of other types of decay. No change in number of nucleons

Answer 12

FALSE: antibonding orbitals are higher in energy than bonding orbitals “Out of phase” electrons that are “repulsive”

Answer 13

Energy is always released when a bond is formed ATP->ADP releases energy because the bonds formed in making ADP releases more energy than what is required to break ATP bonds

Answer 14

Nitrate: NO3- Nitrite: NO2-

Answer 15

Hypochlorite: ClO- Chlorite: ClO2- Chlorate: ClO3- Perchlorate: ClO4-

Answer 16

Balancing reaction: 1. Balance carbons 2. Balance hydrogens 3. Balance oxygens Then do the other atoms

Answer 17

Quick trip for finding high species requires most oxygen to combust: Add 1 for each C, subtract 0.5 for each O Propane: (3x1) - (0x0.5) = 3 Propanol: (3x1) - (1x0.5) = 2.5 Propane requires more energy to combust

Answer 18

Increasing pressure causes shift in reaction towards side with fewer moles of gas

Answer 19

ln[A] vs time | Linear with a slope of -k

Answer 20

Second order reaction

Answer 21

CH3(C=O)CH3 Has ketone group

Answer 22

Combustion —> CO2 + H2O

Answer 23

Do they contain atoms from the same periodic groups?

Answer 24

Groups 1&2 easily replace hydrogen in single replacement Hydrogen gas always produced

Answer 25

Yes: for halide to replace another halide, it must be above it on periodic table (more electronegative)

Answer 26

HCO3 -> CO2 + H2O

Answer 27

CaBr2 + F2 -> CaF2 + Br(g) Fluorine is more electronegative than Bromine so it can replace it

Answer 28

CaSO3 + HCl -> H2SO3 + CaCl H2SO3 dissociates into SO2(g) and H+

Answer 29

H2CO3 -> CO2(g) + H2O

Answer 30

H2SO2 -> SO2(g) + H2O

Answer 31

NH4OH -> NH3(g) + H2O

Answer 32

Sulfide produces H2S(g) in reaction

Answer 33

OH- is a stronger nucleophile than H2O —> negatively charged nucleophile is always stronger than its neutral component

Answer 34

NH3 is a stronger nucleophile than H2O —> N vs O, nucleophilicity decreases L->R on periodic table

Answer 35

Nucleophilicity increases down the periodic table as size and polarizability increase

Answer 36

Bronsted Lowry occurs faster than Lewis Bronsted Lowry: acid is H+ donor Lewis: acid accepts e- pair

Answer 37

PH3 Coordination covalent bond between transition metal with positive oxidation state and atom with lone pair

Answer 38

Small radius and large ionization energy —> high electronegativity

Answer 39

TRUE: some covalent bonds can conduct electricity in solution (HCl)

Answer 40

TEMPERATURE

Answer 41

Flame test = photon emission Solution chemistry = partially filled d orbitals of transition metals

Answer 42

``` M = mol/L (0.8)(0.2L) = 0.16mol of Fe2(SO4)3 ``` There are 3 moles of SO4 in this compound, so 0.16 x 3 = 4.8x10^-1

Answer 43

54-26= 28 neutrons Fe+ also has a 1+ charge So 3 more neutrons than electrons

Answer 44

GC- for 2 liquids with big differences in BP Lower temp = longer retention time = more resolution between peaks

Answer 45

More polar = higher BP

Answer 46

Charge-to-mass ratios

Answer 47

Electron releases photon (light), relaxes to original energy state

Answer 48

pH > pKa = more base than acid

Answer 49

For every 1 unit difference between pKa and pH, ratio of acid/base changes by a factor of 10 For every 2 units, factor of 100... so on...

Answer 50

CO2 buildup in blood causes acidosis Shifts bicarbonate buffer equation right (CO2 is a reactant) CO2 + H2O -> H2CO3 -> H + HCO3

Answer 51

Hydrophobic chromatography- relies on high [salt] to strengthen hydrophobic interactions Decreased [salt] causes proteins to dissociate (weaker interactions)

Answer 52

390-700nm Violet is lowest, red is highest

Answer 53

Trans isomers have higher BP trans are generally more linear, cis do not pack as tightly

Answer 54

Sucrose = glucose (6 membered) + fructose (5 membered)

Answer 55

Large molecules elute first in size exclusion chromatography

Answer 56

Q=AV narrower artery (smaller area due to smaller radius) increases velocity

Answer 57

Dideoxyribose - no 2’ or 3’ hydroxyl

Answer 58

Black body radiators absorb all energy and emit 100% of energy as electromagnetic radiation

Answer 59

Coffee cup- open to atmosphere, so constant pressure. Allows for PV work Bomb calorimeter- sealed, so constant volume. Does not give enthalpy but measures change in interval energy

Answer 60

Isolated system- no exchange with environment Closed system- only energy exchange with environment (deltaE = q + w)

Answer 61

Unstable molecule = high heat of combustion (going from unstable to stable molecule, heat released)

Answer 62

deltaG = deltaH - TdeltaS

Answer 63

acid- produces H+ | Base- produces OH-

Answer 64

Bronsted Lowry- acids donate protons (H+), bases accept protons Lewis- acids accept electrons, bases donate electrons

Answer 65

Adding either an acid or base shifts the equilibrium for ionization of water to the left H2O + H2O <> H3O+ + OH-

Answer 66

HI, HBr, HCl, HNO3, HClO4, HClO3, H2SO4, H3O+

Answer 67

F is too small- cannot spread charge, conjugate base would be unstable

Answer 68

Half equivalence point- middle of nearly horizontal section [HA] = [A-]

Answer 69

Conduction- direct contact Radiation- heat release Not convection (heat rises)

Answer 70

Unstable species = larger negative heat of combustion (going from unstable to stable molecule) F2 (small bond energy) has larger negative heat of combustion

Answer 71

Volume Pressure does not increase entropy (disorder). Think about how increasing pressure of gas creates solid (less disorder)

Answer 72

Q = mc(delta)T 1000J = (0.001kg)c(275-250K) c = 4x10^4 J/kg•K

Answer 73

50 watts = 50 J/s Q = mc(delta)T Q = (1)(4.18)(5) ~ 20 kJ 20kJ = 20,000J x (1 s/ 50J) x (1min/60s) ~7 minutes

Answer 74

Can have all of these High temp can induce fast reaction rate deltaG can be < 0 if temp and entropy increase is high enough Keq can be large- can produce a lot of products at equilibrium, just takes more energy to get there

Answer 75

Low Ka = least acidic HClO is least acidic- conjugate base not as stable (less resonance because less oxygen atoms)

Answer 76

``` Group IA hydroxides (NaOH, KOH, etc) NH2- H- Ca(OH)2 Sr(OH)2 Ba(OH)2 Na2O CaO ```

Answer 77

Boron (B) and beryllium (Be)

Answer 78

“Per- -ate” —> 4 O “-ate” —> 3 O “-ite” —> 2 O “Hypo- -ite” —> 1 O Also: “ate” = “-ic acid” “ite” = “-ous acid” (There are some exceptions)

Answer 79

Lone pair, negative charge, double or triple bond

Answer 80

Atom attached to strong electron withdrawing group, positive charge, carbocation

Answer 81

Carbonyl: C=O Strong electron withdrawing group because O is very electronegative, so C has a partial positive charge Could reduce the nucelophilicity of nearby group

Answer 82

O IS ELECTRON WITHDRAWING

Answer 83

NO. too stable on its own

Answer 84

If it’s really bulky, it can be a base but not a nucleophile

Answer 85

``` Carbocation = electrophile Carbanion = nucleophile ```

Answer 86

Alkyl groups are electron donating, due to dipole moments!

Answer 87

CO2 is always leaving group of decarboxylation. What’s left behind always has a negative charge on the C (nucleophile), can be reacted with further

Answer 88

Count the atom bonded via double bond twice (C=O is like 2 O’s, C=C is like 2 C’s, so C=O would be higher priority)

Answer 89

Leaving group —> carbocation Deprotonation (H) —> carbanion

Answer 90

Lone pairs on top of N, bonded to something below

Answer 91

Co(CH4)4^2+ is NOT a coordinate covalent bond because CH4 doesn’t have a lone pair

Answer 92

Decreasing ionization energy (easier to be IONIZED)

Answer 93

SOLID. Otherwise it would say aqueous calcium

Answer 94

CH3-C=O-CH3

Answer 95

+1 for each C, -0.5 for each O The largest number will require the most O2 to combust

Answer 96

REMOVING PRODUCT temperature affects rate, not yield

Answer 97

Neutron is changed into a proton, an electron is lost

Answer 98

ClO3- One lone pair

Answer 99

4 substituents, 1 lone pair See-saw

Answer 100

3 substituents, 2 lone pairs T shaped

Answer 101

Br is larger so it will be equatorial, Cl will be axial (they can’t both be equatorial when they are cis and adjacent)

Answer 102

NO3- No lone pairs on nitrogen

Answer 103

NO2- One O is double bonded, the other is single bonded and has negative charge N has no formal charge, 1 lone pair

Answer 104

ClO2- One O is double bonded the other carries a negative charge Cl has 2 lone pairs

Answer 105

Decarboxylation (-COOH is removed) Carbanion (negative charge)

Answer 106

Smaller- able to get closer to each other

Answer 107

Sp- 50% s character Sp2- 33% s character Sp3- 25% s character

Answer 108

2 different substances are produced, 1 for each enantiomer

Answer 109

Secondary Creates chiral carbon- 1 H, 1 OH, 1 methyl, 1 R group

Answer 110

Ammonia has lone pair (NH3)

Answer 111

Least separation of charge = major contributor of resonance

Answer 112

Alkenes are electron dense, and so nucleophilic

Answer 113

Positive charge = electron withdrawing

Answer 114

Size- bulky molecule will act as a base

Answer 115

Reduce carbonyl to alcohol while adding R group- lengthen C chain

Answer 116

Carbonyl is replaced with alkene

Answer 117

Strong oxidizing agents

Answer 118

OR- is more basic because carbon chain (R) is weakly electron donating (to O, giving partial negative) while H is neutral

Answer 119

(115x10^-6mol/L)(4.8L)(26g/mol) = 0.014g or 14mg

Answer 120

You’re the same density as water, so just divide your weight in half for half submerged —> 392N

Answer 121

The anion is acetate, the conjugate acid of acetate is acetic acid —> C2H4O2 (extra H) Reduce this to find empirical formula- CH2O

Answer 122

Longer conjugated double bond system, longer the wavelength of visible light that will be absorbed (so lower frequency light)

Answer 123

Uncompetitive inhibitor

Answer 124

Non competitive inhibitor

Answer 125

Affinity of enzyme for its substrate Substrate concentration that will produce initial velocity 1/2 Vmax

Answer 126

Noncompetitive- inhibitor will reduce reaction velocity at any substrate concentration (binds allosteric site) (Competitive inhibitors can be overcome at high substrate concentration)

Answer 127

Oxygen has -2 oxidation state, so to balance out both oxygens, Mn must have oxidation state +4 (Manganese (IV) oxide)

Answer 128

Liver Acetoacetic acid is ketone body, and liver lacks enzyme to convert ketone bodies to ATP (because liver produces ketone bodies when blood glucose is low)

Answer 129

Need MM equation: V0 = (Vmax*[S]) / (Km + [S]) V0 = (2*5)/(15+5) = 0.5uM^-1

Answer 130

FALSE: antibonding orbitals are highest in energy and decrease molecular stability (whether partially or completely filled)

Answer 131

Must be planar, and follow 4n+2 rule (Cis or trans orientation of bonds is irrelevant) 4n+2 rule: count number of pi electrons. 4n+2 will equal number of pi electrons. If you solve for n, it must be a whole number (then it is aromatic)

Answer 132

Count number of pi electrons 4n+2 = number of pi electrons Solve for n, it must be a whole number (Pi electrons: electrons with pi bonds, or lone pairs within p orbitals)

Answer 133

P = force x velocity

Answer 134

Archimedes principle relates to static fluids Bernoulli effect relates to dynamic fluids (like effect of fluid speed on pressure)

Answer 135

E = hc/I E = (6.6x10^-34 x 3x10^8) / (584x10^-9) = 3.4x10^-19J

Answer 136

Aldol addition and condensation reactions proceed under basic conditions by abstraction of the acidic alpha carbon hydrogen Intermediates will have negative charges (so you will NOT have a carbocation) Aldol addition: ketone enolate (nucleophile) and aldehyde (electrophile) produce aldol (C-C bond formed) (Enolate: organic anions from deprotonation of carbonyl compounds)

Answer 137

N=O Smaller atom will be able to get closer Atom size decreases left to right because of electronegativity

Answer 138

SO2 has S double bonded to both O, and a lone pair (doesn’t follow octet) Bent shape

Answer 139

FALSE: tetra substituted alkenes are the MOST stable (low heat of combustion), but ARE more reactive as nucleophiles

Answer 140

Alkenes are NOT electrophiles but HCl is a GREAT electrophile

Answer 141

OR- carbon is more electron donating than hydrogen Cl is a weak base because it is the conjugate base of a strong acid (so it’s stable)

Answer 142

Sigma bond Higher electron density (head-to-head overlap is closer together) HOWEVER a double bond (a pi bond plus a sigma bond) is stronger together than a single bond

Answer 143

Triple bonds (because pi bond is more reactive than sigma bond) Reactivity has to do with tendency of third bond (a pi bond) to react

Answer 144

Trigonal planar or or bent (1 lone pair)

Answer 145

Tetrahedral Trigonal pyramidal (1 lone pair) Bent (2 lone pairs)

Answer 146

Coordinate covalent bond

Answer 147

Boron and beryllium

Answer 148

Third period or higher PCl5, SF6, (PO4)3-, (SO4)2-

Answer 149

Benzene ring as functional group

Answer 150

R1R2-C=N-R3 N has a lone pair

Answer 151

S double bonded to 2 O’s, and single bonded to 2 R groups

Answer 152

Hemiacetal: Alcohol and ether attached to the same carbon Acetal: 2 ethers attached to same carbon

Answer 153

Hemiketal: An alcohol and an ether attached the same carbon, along with 2 other carbons Ketal: 2 ethers attached to same carbon, along with 2 other carbons

Answer 154

Clockwise, +

Answer 155

Z = same side (cis) E = opposite side (trans)

Answer 156

Bases abstract protons (hydrogens) Nucleophiles attack carbons (or other central atoms)

Answer 157

Basicity —> thermodynamics (compares stability of reacted and unreacted base) Nucelophilicity —> kinetics (rate at which it reacts with electrophile)

Answer 158

TRUE. Has high energy of activation

Answer 159

Syn addition (H bonds added on same side)

Answer 160

Yes. Pi electrons in double bond will attack electrophiles (leave behind carbocation)

Answer 161

Nucleophile- lone pair acts as Lewis base Lewis acid- when oxidized to carbonyl group, oxygen accepts pairs of electrons from the OH bond as proton is abstracted

Answer 162

Less substituted alcohols are more acidic Tertiary alcohols are destabilized by induction

Answer 163

Primary alcohol -> aldehyde -> carboxylic acid

Answer 164

NaBH4- aldehydes and ketones LiAlH4 or H2/pressure- aldehydes, ketones, carboxylic acids, esters (stronger reagent) LiAlH4 produces 2 equivalent of H-, NaBH4 only produces 1

Answer 165

Ketone or aldehyde “Vic”= adjacent (2 adjacent hydroxyl groups) Carbons with functional groups must be tri- or tetra- substituted —> tri = aldehyde —> tetra = ketone

Answer 166

They make great leaving groups

Answer 167

SN2 Alcohol attacks tosyl/mesyl halide (kicks off halide)

Answer 168

Alkene- hot, concentrated acid | Alcohol- cold, dilute acid

Answer 169

Grignard synthesis RMgX (usually RMgBr)

Answer 170

R-O-R NOT reactive EXCELLENT solvent

Answer 171

Alkenes are weakly electron withdrawing

Answer 172

When peroxides are present

Answer 173

molecule with least negative heat of combustion or smallest bond energy = least stable = highest heat of combustion

Answer 174

Buffer- weak acid/weak base or strong acid/ strong base Titration- weak acid/strong base or weak base/strong acid

Answer 175

Equilibrium constant specific for solubility

Answer 176

Fatty acid. Hydrophobic carbon chain and acidic group

Answer 177

Carboxylic acid OH

Answer 178

Carbonyl (C=O)

Answer 179

Conjugated C=C (like in benzene)

Answer 180

High affinity binding (Ka > 1)

Answer 181

1s2 2s2 2p6 3s2 3p6 4s0 3d10 4s subshell has highest principle quantum number so it empties first

Answer 182

Max number of electrons allowed in a shell = 2n^2 So if n=3 .... 18 electrons

Answer 183

Max number of electrons in a subshell = 4l+2 So in 4th subshell, l=4 So... 18 electrons

Answer 184

Elements on the end of a block (s, p, d, f block)

Answer 185

E = hf c = f x wavelength ... E = hc/wavelength

Answer 186

Difference in energy is function of: [1/ni^2 - 1/nf^2] So there’s a greater energy difference between 1 and 2 shells (1/1 - 1/4) vs (1/9 - 1/16)

Answer 187

``` n = 3 l = 0,1,2 ml = -2,-1,0,1,2 ms = +/-1/2 ```

Answer 188

The lower the sum of n and l value, the lower the energy

Answer 189

Remove electrons from subshells with highest n value first

Answer 190

In given subshell, orbitals are filled to give max number of half filled orbitals with parallel spins (Like avoiding sitting next to someone on a bus)

Answer 191

Paramagnetic- has unpaired electrons

Answer 192

``` s block- only highest s subshell (Group I And II) p block- highest s and p subshells (Group 13-18) d block- highest s and d subshells (Transition) f block- highest s and f subshells (Lanthanides and actinide) ```

Answer 193

CO2- least polar compounds travel further, have larger Rf TLC has nonpolar solvent, capillary action will pull eluent up—> more soluble eluent will travel farther

Answer 194

Rf- distance travelled by solute/ distance travelled by nonpolar solvent Benzyl ester (other two are polar alcohols) Nonpolar solvent in TLC, capillary action pulls eluent up the plate- nonpolar travel farther—> larger Rf value

Answer 195

Different charges ClO4- (perchlorate) has one negative charge PO4^3- (phosphate) has 3 negative charges

Answer 196

Hydrogen bonding!

Answer 197

Energy is released Shells farther from the nucleus will have lower ionization energies. To move to a shell closer to the nucleus (one with higher ionization energy, more stable), energy is released

Answer 198

8 —> amide hydrogen would be highly deshielded by electronegative nitrogen Deshielded = downstream (higher number)

Answer 199

Not likely, weak bases not readily protonated

Answer 200

Acidic or basic, but acidic easier Basic amide hydrolysis requires strong base/heat

Answer 201

Amides + H3O+/heat —> carboxylic acid + amine (R-NH-R) Reverse is condensation reaction: Carboxylic acid + amine —> amide + water

Answer 202

pKa Acid-base equilibrium constant is Ka

Answer 203

NH3 Has a lone pair Weak base

Answer 204

Lewis bases must have lone pair of electrons to donate to Lewis acid Bronsted bases accept protons

Answer 205

Double bond formed

Answer 206

Inverse Increase molecule mass, decrease freezing point

Answer 207

Basic Acetate ion is a proton acceptor (conjugate base of a weak acid is itself a weak base)

Answer 208

Hydrogen with metal: -1 | Oxygen in peroxide’s: -1

Answer 209

N: -3 H: +1 S: +6 O: -2

Answer 210

Fe: +2 C: +4 O: -2

Answer 211

Species really wants to be reduced- wants electrons Negative E*- less likely to gain electrons than hydrogen ions (Hydrogen Half-Cell is standard comparison)

Answer 212

FALSE: can be spontaneously reduced if paired with another species with more negative electric potential

Answer 213

... the half reaction of the species with the lowest reduction potential and take the negative of its E value (this is the oxidation potential) DON’T USE STOICHIOMETRY. moles don’t matter here

Answer 214

Galvanic- (+) cathode/ (-) anode, cell potential is always positive, can be created using any two metals (current spontaneously generated) Electrolytic- external voltage applies to galvanic cell which forces electrons to flow in opposite direction (-) cathode/ (+) anode, cell potential is always negative, lower reduction potential species is reduced. Sum of external voltage and negative cell potential must be positive Both- REDUCTION AT CATHODE, oxidation at anode

Answer 215

Neutralizes charge buildup; allows electron flow to continue

Answer 216

Electric potential of concentration cell is always 0 | Always positive for galvanic cell, negative for electrolytic cell

Answer 217

Galvanic is positive. My GALS are always POSITIVE Electrolytic is negative. ELECTRONS are NEGATIVE

Answer 218

deltaG* = -nFE* Where n is number of moles of electrons transferred in redox rxn F is faradays constant (the charge on one mole of electrons- 6x10^23 x 1.6x10^-19 = 9.6x10^4) E* is electric potential So positive electric potential = negative free energy change = spontaneous

Answer 219

PV=nRT R = 0.08 L*atm/mol*K or 8.3J/mol*K

Answer 220

Gas molecules have no volume and no intermolecular forces

Answer 221

``` P = 1 atm V = 22.4 L n = 1 mole R = 0.08L*atm/mol*K or 8.3J/mol*K T = 273 K (0* C) ```

Answer 222

P1V1/T1 = P2V2/T2 Helpful because R is constant, can be used when given same number of moles of gas

Answer 223

Decreases pressure PV/nRT < 1 Due to intermolecular forces assumption—> at low temperature, pressure is decreased

Answer 224

Increased molecular volume increases volume in real gases PV/nRT > 1 Ar high pressure, molecules are pushed close together and their actual size begins to matter- becomes comparable to the distance between them

Answer 225

Deposition

Answer 226

On a phase diagram, occurs past the critical point- liquid and gas phase merge. No heat of vaporization at critical point.

Answer 227

FALSE: can be seen by differing slopes on heating curve

Answer 228

Phase change. All energy goes towards phase change, so no change in heat

Answer 229

Evaporation- only some intermolecular forces broken in melting, all broken in evaporation to form gas

Answer 230

Increase temp, increase Vp Liquid boils when Vp = Patm Must increase temp to cause boiling

Answer 231

Addition of anything decreases Vp More intermolecular forces to be broken

Answer 232

... partial pressure of that gas over that liquid

Answer 233

FALSE- no intermolecular forces (ideally) in gas so it doesn’t matter

Answer 234

RECEIVING water has HIGHER osmotic pressure

Answer 235

Osmotic pressure = iMRT i is # of ions formes in solution (van’t hoff) M is molarity

Answer 236

colloids- solvents with very small un dissolved particles

Answer 237

Inorganic compound in water in which water molecules are permanently bound into crystalline structure

Answer 238

``` Molarity = mol/L Molality = mol/kg ```

Answer 239

Temperature (same as with Keq, Ka, Kb)

Answer 240

those containing: Nitrate (NO3) ammonium (NH4+) GroupIA metals

Answer 241

``` Those containing: Carbonate (CO3^-2) Phosphate (PO4^-3) Silver Mercury Lead ```

Answer 242

Vicinal diols

Answer 243

Metals- large atomic radius, small ionic radius Nonmetals- small atomic radius, large ionic radius.

Answer 244

Electrostatic attraction- measure of net positive charge experienced by valence electrons Increases left to right More or less constant in a group because of increased electron shielding down a group (from increased principal quantum number- valence electrons are increasingly separated from nucleus by more energy shells)

Answer 245

Zeff increases left to right So atomic radius decreases left to right Atomic radius also increases down a group (larger principal quantum number n)

Answer 246

Ionization energy- energy required to remove electron Electron affinity- energy dissipates when an electron is gained (opposite concept of ionization energy) Electronegativity- attractive force an atom exerts on electron in a chemical bond

Answer 247

``` Hydrogen (2) Helium (2) Lithium (2) Beryllium (4) Boron (6) ```

Answer 248

Much higher for ionic- strong bonding

Answer 249

Formal charger- underestimate Oxidation number- overestimate

Answer 250

Larger = more polarizable

Answer 251

Nucleophile- electrophile Lewis acid-base Complexation

Answer 252

2 Normality often used for hydrogen ion concentration Normality always assumes rxn goes to completion

Answer 253

Normality / n = molarity Where n is number of whatever you’re looking for (protons, ion, electrons, etc)

Answer 254

The lITEst anions have fewest oxygen The heaviest anions ATE the most oxygens Ex: nitrite = NO2-, nitrate = NO3-

Answer 255

Have high oxidation numbers on the metal, so tend to gain electrons to lower this Ex- MnO4- (permanganate), CrO4^2- (chromate)

Answer 256

Number of e- transferred = | Oxidation # of product - oxidation # of reactant

Answer 257

R = 0.082L*atm/mol*K is basically in units of volume*pressure/mol*temperature —> use for PV=nRT R = 8.314 J/mol*K includes a unit for energy —> deltaG = RTlnK (energy)

Answer 258

Nitrates (NO3-) Acetate (CH3OO- or C2H3O2-) Group 1 Sulfates (SO4^2-, except when paired with Ca2+, Sr2+, Ba2+, Ag+, Pb2+) Ammonium (NH4+) Group 17 NOT SOLUBLE: Pb (lead) Mg (Mercury) Si (silver, Ag2+)

Answer 259

CO3^2- is NOT soluble except when paired with group 1 or ammonium Phosphates (PO4^3-) follow same rule

Answer 260

Rates of velocities of gas diffusion is proportional to the inverse of the ratio of the square roots of the molar masses VA = sqrt(B MW) —- —————- VB = sqrt (A MW) À will travel faster (small mw)

Answer 261

All solutions expand in volume when heated Molarity will increase with temperature

Answer 262

Ammonium and nitrate are always soluble Sulfate (SO4^2-) is usually soluble except when with Ca2+, Ba2+, Sr2+, Hg2+, Pb2+, Ag2+

Answer 263

KE of molecule exceeds intermolecular forces

Answer 264

Dipole bonds Dipolar bonds oscillate at specific vibrational frequency- determined by strength of bond and molecular weight

Answer 265

stronger bond and higher mw = higher frequency Roughly follows Hooke’s law, F=km where strength is like k, mw is like m

Answer 266

Carbonyl, C=O: 1700 sharp, deep Saturated alkane: 2800 sharp, deep Amine, NH: 3300 broad, shallow Amide, NH: 3300 broad, deep Nitrile, C[triple]N: 2250 sharp, deep

Answer 267

More conjugation = farther to the right on absorption scale- at a higher wavelength

Answer 268

Double and triple absorb strongly (triple more than double) Single bonds will not Electrons absorb energy from radiation and excite to next energy level- absorption is measured

Answer 269

Most common fragment, usually most stable

Answer 270

Odd atomic number or odd mass number These atoms have nuclear spin, which creates magnetic field (Same for MRI, basically NMR on human body)

Answer 271

n + 1 sub peaks, where n is number of non-equivalent hydrogen neighbors Number of hydrogens presented by that peak is # of sub peaks - 1

Answer 272

Upfield = shielded Downfield = Deshielded

Answer 273

Gives molecules charge- more soluble in aqueous layer

Answer 274

Nonpolar layer is less dense than water- on top Polar products are in bottom

Answer 275

Difficult to evaporate off the solvent to obtain the product

Answer 276

Vacuum drives pressure down to meet vapor pressure Liquids boil when P = Patm Lowers boiling point- good for substances with high boiling points

Answer 277

Nonpolar Number close to 1 means polarity of component is similar to solvent (which is usually nonpolar)

Answer 278

Product dissolved in minimum amount of hot solvent Solution cooled slow as possible- if temp is dropped just below melting point of product, crystals will form and impurities will remain in solution

Answer 279

Partial positive on carbon

Answer 280

ACIDIC Due to resonance stabilization (alpha carbon is that on carbon adjacent to carbonyl carbon) of conjugate base When 2 carbonyls separated by single carbon, the hydrogens on middle carbon are VERY acidic (partial positive of carbonyl carbons)

Answer 281

Donating groups decrease reactivity (less partial positive) Withdrawing groups increase reactivity (less electron dense- most partial positive) Bulky groups decrease reactivity (steric hinderance)

Answer 282

Recipients only

Answer 283

Ketone or aldehyde

Answer 284

Electrophiles- carbonyl carbon with positive charge is attached by nucleophile

Answer 285

Aldehydes/ketones undergo nucleophilic addition Carboxylic acid/ amides/ esters/ anhydrides undergo nucleophilic substitution (need a leaving group to undergo substitution) Aldehydes/ketones leaving group would be a strong base- BAD leaving group

Answer 286

Accept electrons when a base abstracts an alpha hydrogen (on carbon adjacent to carbonyl carbon)

Answer 287

Alpha hydrogen adjacent to aldehyde/ketone becomes bonded to carbonyl oxygen Double bond is switched from C=O to bond between carbonyl carbon and alpha carbon

Answer 288

Keto- sum of bond energies is greater (C=O in keto vs C=C in enol)

Answer 289

Acetals/ketals: 2 -OR groups Hemiacetal/ketals: 1 -OR group And 1 -OH group

Answer 290

Alcohol is nucleophile- attacks carbonyl carbon, pushes pi e- from C=O to oxygen Negatively charged O is protonated, original alcohol deprotonated to form ether Alcohol protonated again to form leaving group - water Deprotonation of second alcohol gives another ether, yielding either acetal (from aldehyde) or ketal (from ketone)

Answer 291

Conversion to acetal (aldehyde) or ketal (ketone) using alcohol (diols best) Acidic conditions reverses this

Answer 292

CarbANION carbanion attacks diatomic halogen

Answer 293

Condensation of aldehyde or ketone with another aldehyde or ketone 1. Base abstracts alpha H 2. carbANION attacks any carbonyl carbon 3. Oxygen protonated—> alcohol

Answer 294

One carbon in between carbonyl carbon and carbon bearing hydroxyl group (C=O and C-OH)

Answer 295

Aldehyde or ketone with double bond between alpha and beta carbons Electrophile- carbonyl is electron withdrawing (partial positive)

Answer 296

HCOOH basically carboxyl acid with a hydrogen group

Answer 297

CH3COOH carboxylic acid with methyl group

Answer 298

C6H5COOH Carboxylic acid on benzene ring

Answer 299

Yes! Twice! To form dimers. Though dimers actually don’t have a net dipole despite being very polar, so slightly soluble in nonpolar substances (as a dimers only)

Answer 300

RCOOH2+ + Nu:- | —> RCONu + H2O

Answer 301

Loss of CO2 from beta-keto carboxylic acid Leaves behind resonance stabilized carbANION BASE catalyst Carboxylate ion usually retakes hydrogen from base to from keto-enol tautomer

Answer 302

Estérification (alcohol And carboxylic acid) RCOOH + ROH —> RCOOR + H2O Forms ester Requires ACID catalyst (because hydroxyl must become water to be good leaving group)

Answer 303

PCl3 PCl5 SOCl2

Answer 304

Cl- is more stable than -OH, so makes better leaving group

Answer 305

Acid chloride- most reactive (Cl- is really good leaving group, Cl is strongly withdrawing and makes partial positive on carbonyl strong) Amides- least reactive/most stable (NH2 is strong base and so BAD leaving group)

Answer 306

Anhydride RC(=O)OC(=O)R

Answer 307

RC(=O)NH2 Amide

Answer 308

RCOOH carboxylic acid

Answer 309

RCOR ester

Answer 310

Anhydride is ester where -R group is carbonyl R-C(=O)-O-C(=O)-R

Answer 311

GREAT electrophiles 2 carbonyl carbons are highly reactive to nucleophile because leaving group is resonance stabilized carboxylate ion

Answer 312

Amide: R-C(=O)-NH-R Amine: R-NH2

Answer 313

N in amide donates electrons via resonance- closer to Sp2 because of partial double bond character

Answer 314

Amines more basic Amides N has less electron density because of partial double bond character and partial positive of carbonyl

Answer 315

Primary amides react in strong, basic solutions of Cl2 or Br2 to form primary amines Mechanism includes decarboxylation- shortens chain Allows you to add amine to a tertiary carbon

Answer 316

Recipients only

Answer 317

Hydrolysis of ester gives alcohol and salt of carboxylic acid 1. Hydroxide ion attacks carbonyl carbon 2. Electrons go up to oxygen but fall back down and kick off -OR 3. Either -OR or hydroxide ion abstracts carboxylic acid hydrogen—> carboxylic ion, which Na+ or K+ associates with (soap)

Answer 318

Use Beta keto ester to make ketone Beta keto ester: -C(=O)-CH2-C(=O)-O- Hot acid causes loss of COOR group to get ketone

Answer 319

Triphosphate- ATP, GTP, UTP Diphosphate- FADH2, NADH monophosphate- FMN, DNA, RNA

Answer 320

Ammonium- electrophile | Ammonia- nucleophile

Answer 321

R-C(=NR)-R/H

Answer 322

SN2 Kicks or halide, halide ion acts as base and abstracts H NH3 + CH3Br —> NH2CH3 + HBr

Answer 323

Formation of primary amine from primary alkyl halide, but avoids side reactions of alkyl amine synthesis

Answer 324

LiAlH4 NaBH4 H2/ catalyst with pressure

Answer 325

Primary amine —> imine Imine: R-C(=NR)-R Secondary amine —> enamine Enamine: R2C=C(-NR2)R Tertiary amine do not react (steric hinderance, will be a base not a nucleophile)

Answer 326

Oxygen. Repulsion from additional electron in already half filled 2p orbital Ionization energy: N>O>C

Answer 327

Side to side overlap of 2 p orbitals

Answer 328

Both sigma bonds

Answer 329

All groups on right are below plane, all groups on left are above plane Hydroxyl group on next-to-last carbon will be nucleophile that attacks the aldehyde carbonyl during ring closing Start with linear projection, so If the answers are Fischer projections try each one

Answer 330

0.5 mol of each, but AgNO3 is used at twice the rate So Na2S will be excess, and only half will be used, so 0.25 mol will be left

Answer 331

1:3 molar ratio | So you would need 6 mol H2 to react with 2 mol Au2S, but you only have 5, so H2 is limiting reagent

Answer 332

SF4- 4 groups + 1 lone pair = see-saw (2 groups act as base of seesaw, 2 groups make the board, lone pair on top) BrF3- 3 groups + 2 lone pairs = T shaped (2 lone pairs push groups done to make a T)

Answer 333

3 formal charges NO3-, N has NO lone pairs

Answer 334

NO2- | One O is negative the other is double bonded. N has 3 bonds, no formal charge (0)

Answer 335

ClO2-, one O is negative the other is double bonded Cl has 2 lone pairs, 2 bonded O Gives sp3 (2 groups) and bent shape

Answer 336

Differ at only one chirality center

Answer 337

Opposite R/S at all pairs of chiral carbons across plane of symmetry but groups must be in SAME stereochemical configuration (same side of plane)

Answer 338

1 lone pairs + 2 double bonded O

Answer 339

Enantiomers 2 different substances produced for each enantiomer

Answer 340

Monosubstituted alkene Less stable molecule has higher heat of combustion (more reactive, more energy)

Answer 341

Carbonyl C in acetaldehyde (more acidic alpha H) is stronger e- withdrawing group than carbonyl C in acetone This makes the carbanion more stable in acetaldehyde (stronger partial positive pulling electrons)

Answer 342

Molecules with negative charges donate electrons. Species that donates electrons via hyperconjugation will have positive formal charge after attachment. WILL: -NH2, -SH WILL NOT: -NO2, -CHCH2 (alkene- electron withdrawing), -NH3 —> these will all have positive formal charges

Answer 343

Having e- withdrawing groups decreases basicity, e- donating groups increase basicity NH2COOH < NH3 < N(CH3)3

Answer 344

Aldehyde- relatively acidic alpha H Amine with abstracted H is a strong base itself- so amine is weak acid that doesn’t want to give up H

Answer 345

Dimethylamine is bulky, acts as a base in E2 Single step rxn to abstract H from chlorocyclohexane

Answer 346

E2 SN2 requires strong nucleophile for back side attack (bulky bases can’t be strong nucleophile because steric hinderance)

Answer 347

Grignard- reduces carbonyl to alcohol while adding R group to lengthen chain LiAlH4 would add H, not methyl (not lengthen chain) Wittig- replace carbonyl with alkene Jones- strong oxidizing agent

Answer 348

Replaces carbonyl with alkene

Answer 349

Strong oxidizer

Answer 350

Increase in pressure associated with increase in partial pressures of each gas System moves towards side with fewer moles of gas

Answer 351

Temperature changes Keq, so Q (reaction quotient) is no longer the same as Keq

Answer 352

Kinetic But thermodynamic products are more stable (more negative deltaG)

Answer 353

First law: deltaU = Q - W Temperature and internal energy are directly proportional, so U is constant So Q = W aka heat added to system equals work done by system Hyperbolic curve on PV

Answer 354

First law: deltaU = Q - W Adiabatic- no heat exchange between system and environment Q = O So deltaU = -W Hyperbolic on PV

Answer 355

Does not affect first law (deltaU = Q - W) But will be a flat line on PV curve

Answer 356

First law: deltaU = Q - W Isochoric = isovolumetric Gas doesn’t expand or compress (no change in volume) so no work is performed deltaU = Q Vertical line on PV

Answer 357

Standard: 25C (298K), 1 atm, 1M Used for kinetics, equilibrium, thermodynamics STP: 0C (273K), 1 atm For ideal gases

Answer 358

Endothermic process Liquid is the heat source, so liquid temp actually decreases But obviously liquid receives thermal energy itself from another source

Answer 359

Sublimation To purify product that is heated under reduced pressure. Pure product is more volatile than impurities

Answer 360

Liquid heated in closed system decreases in density Density of vapor above increases Liquid/ gas densities become equal so there is no distinction between phases Heat of vaporization = 0

Answer 361

State function- path independent, but may be dependent on each other Process function- define the path (Q and W)

Answer 362

Coffee cup- constant pressure (Patm) Bomb- constant volume

Answer 363

Enthalpy changes of reactions are additive

Answer 364

Combustion C6H12O6 + 6O2 -> 6CO2 + 6H2O

Answer 365

deltaHrxn = bonds broken - bonds formed Breaking bonds is endothermic, forming bonds is exothermic

Answer 366

Energy spontaneously disperses (increase in entropy)

Answer 367

Spontaneous Free energy change is irrespective of enthalpy

Answer 368

Activation energy Not free energy change. Spontaneous reactions can be fast or slow

Answer 369

Major product at first will be the one that forms quicker- kinetic product (under kinetic control) Given enough time, thermodynamic (more stable) product dominates- under thermodynamic control. Lower free energy value

Answer 370

Heat transfer- use calorimeter

Answer 371

Endo/exothermic Endergonic/ exergonic describe free energy and cannot be determined by reaction coordinate

Answer 372

Deposition Solid-> gas

Answer 373

Movement of proton (H+) and its electrons (e- in a double bond)

Answer 374

Acid: carbonyl attacks acid proton, then conjugate base of acid attacks alpha H —> get an enol (R-C(OH)=C-R) Base: base attacks alpha H and double bond is moved from carbonyl to C=C (concerted to avoid 5 bonds on carbon) —> get an enolate (R-C(O)=C-R). Enolate becomes protonated at oxygen—> get an enol ALWAYS deprotonate alpha H

Answer 375

Fructose Can get glucose from fructose via keto-enol tautomerization

Answer 376

Water (or weak acid) carries H from one O to the other O Alcohol causes addition of R group (need 2 equivalents of alcohol to get both R groups). Alcohol attacks carbonyl carbon (partial positive charge because of e- withdrawing carbonyl group)

Answer 377

Protonate it! Might see H+ added into reaction RC(=OH+)R is more reactive

Answer 378

``` Carbon 3 Glucose: CHO H———OH OH——-H H———OH H———OH CH2OH ```

Answer 379

Epimers Carbon 2 reversed instead of carbon 3 (glucose) Remember: Mannose, Mountain, one above glucose switched carbon

Answer 380

Glucose + galactose (both 6 membered) Beta-1,4-glycosidic bond

Answer 381

Glucose (6C) + fructose (5C) Alpha-1,2-glycosidic bond

Answer 382

Glucose monomers Alpha-1,4-glycosidic bonds Linear- amylose Branched- amylopectin

Answer 383

Both made of glucose polymers Starch- alpha-1,4 Cellulose- beta-1,4

Answer 384

NH3 < 3* < 1* < 2* Tertiary is too bulky SN1 takes 3* bases not because it is preferred but because 3* bases CANNOT do SN2 (requires backside attack)

Answer 385

:Nuc attacks either at carbonyl carbon or beta carbon- 2 away (depends where the positive charge ends up in resonance structure) Double bond is always between alpha and beta carbons Alpha-beta unsaturated carbonyls make good reactive species

Answer 386

Attacks beta carbon —> 1,2 addition Attacks carbonyl carbon —> 1,4 addition Either way, H adds to O and :Nuc adds to C

Answer 387

Grignard- lengthens chain with R group (RMgBr, ether 2) H3O+) NaBH4 or LiAlH4- add H These usually all occur via 1,2 addition

Answer 388

Something with electrons (double/ triple bond) adds to something else Ex, C=C adds to H2O to make C(OH)-C(H)

Answer 389

Primary amine attacks carbonyl, gives you imine (like replacing O in carbonyl with N-R) Secondary amine attacks carbonyl, gives you enamine (add N-R where O was in carbonyl, but put double bond between carbonyl C and alpha C) Secondary amines have an R group instead of a second H group, so no H to be deprotonated to from double bond. Tertiary amines have no H at all to be deprotonated, so won’t react

Answer 390

Only chiral C on chain (non chiral go on end) Designate first wedge/dash as L/R, then reverse each carbon For cyclic, all up on one side/ all down on other side (break the cyclic molecule). Last R group goes in direction the end molecule (on the top or bottom of Fischer) was pointed in the cycle

Answer 391

Higher blood oxygen because of increased solubility because of increased partial pressure

Answer 392

Both High pressure and low temperature- volume is less than ideal due to significant intermolecular forces As gas approaches condensation pressure/ temperature

Answer 393

20. 2g / 22.4L = 0.9 | 22. 4 L is STP volume

Answer 394

P = (density)RT —————— M M is molar mass

Answer 395

Intermolecular forces- H bonding

Answer 396

Alcohol Rearrangement may occur to produce more stable carbocation via methyl shift

Answer 397

Will always be a new bond between the carbonyl C and the C next to the Mg

Answer 398

MgCl can attack carbonyl of aldehyde and cause addition. Carbonyl becomes an oxygen This is example of Grignard reaction

Answer 399

Carboxylic acid

Answer 400

Ketone No other H to be oxidized if it’s secondary

Answer 401

Primary alcohol LiAlH4 is strong reducing agent

Answer 402

Vic-diol: alcohols on adjacent carbons First step: spontaneous dissociation of one protonated alcohol. Then followed by methyl shift- other alcohols H is abstracted and carbonyl forms (final product)

Answer 403

Aldehydes < alcohols < water < carboxylic acid Waters conjugate base is more stable then alcohols

Answer 404

Imine is basically carbonyl with NH/NR instead of O Carbonyl is more reactive because C=O is more polar than C=N

Answer 405

Beta-keto acid: ketone on the beta carbon of a carboxylic acid (2 C away) Base abstracts H on beta-keto acid and the electrons collapse down to form a double bond to the C. The bond between the carbonyl carbon and alpha carbon is broken —> decarboxylation This leaves carbanion on alpha carbon that is stabilized by resonance onto neighboring ketone. This will be protonated in solution. Final product- ketone and CO2

Answer 406

Resonance Induction helps but not as important

Answer 407

Yes, into imines Enamine: double bond on C=C, not amine group Imine: double bond between C=N React NH4+ with imine- nitrogen attacks H in ammonium, and C=N gives electrons to N while NH3 pulls H from methyl group, causing double bond to form between C=C

Answer 408

Keto (electrophilic) + water -> water protonates C=O so double bond shifts down to C=C to remove positive charge on O -> now you have enol (nucleophilic)

Answer 409

HOCH2CH2OH (diol)- can react with carbonyls to form cyclic structures that can be easily reversed by acid Tosyl chloride is electrophile and so is carbonyl- won’t react Grignard reduces carbonyl to alcohol, not easily reversed

Answer 410

Tosyl chloride (electrophile)- commonly used to protect alcohols and other nucleophiles Alcohol attacks tosyl chloride

Answer 411

2-butanone: ketone on carbon 2 (4 carbons total) The hydrogen will be abstracted from C1- there are not R groups (only H) C3 has weakly donating R groups (CH2) so the carbanion will be unstable Aldol condensation: condensation of one aldehyde or ketone with another.

Answer 412

Acyl (acid) chloride: -COCl PCl3, PCl5, SOCl2 (strong halide reagents)

Answer 413

Imine: RC(=NH/R)R LiAlH4: strong reducing agent Hydride ion produced by LiAlH4 attacks partial positive carbon and kicks double bond (of C=N) onto nitrogen—> intermediate is nitrogen anion. Final product is primary benzyl amine (becomes protonated)

Answer 414

Sulfur will attack carbonyl carbon. Double bond will push electrons up to oxygen. Oxyanion will be protonated to create water, which will leave. The product is a thioketone- R2C=S

Answer 415

Hydrazine (nucleophile) attacks carbonyl (electrophile) and causes addition of hydrazine to carbonyl carbon

Answer 416

Transform ketone into acetal. Acid work up will return acetal to ketone Acetal: two -OR groups on same carbon, that carbon being attached to another R group and an H (ketal would be 2 more R groups)

Answer 417

Excess alcohol would give 2 -OR groups—> an acetal

Answer 418

Tertiary, sterically hindered Groups that induce induction—> stable carbocation Br (leaving group) will leave first, then nucleophile will add to carbocation—> SN1

Answer 419

Saponification. Basic hydrolysis of ester

Answer 420

Carboxylic acid

Answer 421

RCONH2 (amide) can only be reduced to primary amine by LiAlH4 Nitro groups (RNO2), nitriles, and imines (R2C=NH) can be reduced to primary amines by all common reducing agents

Answer 422

No, if you have a carbonyl double bond that can act as a nucleophile, it can abstract H from neighboring carboxylic acid to form enol Enol: double bond on C=C (carbonyl C and alpha C) Reminder: decarboxylation forms keto-enol tautomer and CO2

Answer 423

Keto: has C=O Enol: has C-OH (Enolate: has C=C below O-, between carbonyl and alpha C) Ketal: 2 -OR groups, 2 R groups Acetal: 2 -OR groups, 1 R group, 1 H

Answer 424

CH3-CH2-CO-CO-OH (Ketone next to carboxylic acid) Oxo = ketone For hydroxybutanoic acid: replace ketone group with hydroxyl

Answer 425

3-oxybutanoic acid will In order to undergo decarboxylation, must be resonance to stabilize carbanion- ketone must be in beta position

Answer 426

Amine (RNH2)- nucleophile Acid chloride and ammonium are both electrophiles Amides (RCONHR) won’t react with anything at carbonyl carbon and H on amide N are not acidic Reminder: Lewis acids are electrophiles, Lewis bases are nucleophiles

Answer 427

Amide (RCONHR) are to amines (RNH2) what esters (RCOOR) to alcohols (ROH)

Answer 428

Causes condensation of component with higher boiling point by increasing surface area for condensation

Answer 429

Boiling point

Answer 430

Phenol: benzene + OH Aniline: benzene + amine (NH2) These can H bond Benzoic acid: benzene + carboxylic acid Toluene: benzene + methyl

Answer 431

FALSE. Strength of magnetic field is not varied, but frequency of external electromagnetic radiation (usually radio) is. H-NMR absorbances created by nuclear energy transition- transition of nucleus from with the field to against it

Answer 432

UV- electron excitement IR- intramolecular vibrations

Answer 433

NMR depends on nuclear spin which is zeroed out if there is an even number of protons+neutrons

Answer 434

Amines are very shallow (3300-3000 region) Amides are deep, not a smooth bottom like alcohol (3700-3500). Amides also have carbonyl at 1700

Answer 435

Acid anhydride: RC(O)OC(O)R Acid anhydride + amine —> amide (RC(O)NHR)

Answer 436

Carboxylic acid

Answer 437

Ester (RCOOR)

Answer 438

Acid anhydride

Answer 439

Ketone | Cl replaced by R group

Answer 440

Amide | Cl replaced by NH2

Answer 441

External magnetic field gradually increases so all species fragments (of different mass to charge ratios) hit detector

Answer 442

Highest mass/charge ratio will hit last- heaviest will have slowest acceleration

Answer 443

Ketone- ester has resonance that creates double bond with carbonyl carbon between C=OR, so the oxygen donates electrons to carbonyl carbon, making it less electrophilic

Answer 444

Normality = [acid or base equivalents] x equivalents H2SO4 is two diprotic acid N = [2](2) = 4

Answer 445

GEW = (g/mol) x (mol polyvalent/ # of equivalents) Phosphoric acid is triprotic acid GEW = (98)(1 mol/ 3 H+ equivalents) = 33g/ H+ equivalent

Answer 446

K2CO3 -> 2K+ + CO3^2- CO3^2- + 2H2O -> H2CO3 + 2OH- K2CO3 is dibasic 0.4L x (1 equivalent H2O/ 1 L H2O) x (1 mol K2CO3/ 2 equivalents H+) x (138g/mol) = 27.6 g

Answer 447

Buffering capacity is 3x, and pH will stay same pH = pKa + log([A-]/[HA]) Ratio is same, so pH is same Buffering capacity is 3x because there are more molecules of H3O+ to neutralize OH-. Not 6x increase because conjugate base doesn’t contain H3O+ ions

Answer 448

Act as buffer- neutralizes H2SO4 by bicarbonate (NaHCO3 dissociates)

Answer 449

Bronsted Lowry base: accepts H ion (note Cl- ion) Lewis acid: donates electron pair Arrhenius base: increases [OH-]

Answer 450

Ka = [H+][A-]/ [HA] Ka = x^2 / (molarity - x) “-x” can be considered negligible Solve.

Answer 451

Half equivalence point- point of neutralization. pH = pKa

Answer 452

Ester Acyl halide is carbonyl with halide (like ketone where one R group is halide) C of acyl halide is electrophile. Alcohol (:Nuc) attacks/ pushes electrons onto O. Double bond reformed by kicking off halide (good leaving group). O from alcohol loses protons, so left with an ester (like a ketone where one R group is OR)

Answer 453

Central cation bound to same ligand in multiple places

Answer 454

(MV)1 = (MV)2

Answer 455

Mole fraction: Find mol of NaCl, divide by mole of (NaCl + water) Water would be 1000g (density = 1g/mL) Percent composition by mass: Divide 90g NaCl by (90+1000) total grams

Answer 456

Ion product (IP) is analogous to reaction quotient (Q)

Answer 457

P = XP* where X is mole fraction of solvent and P* is vapor pressure in pure state Density of water at 100*C = 1g/mol, pressure will be 1 atm (because it’s at boiling point) 0.18L = 180g -> /18 = 10 mol water Mole fraction of water = 10/12(total) ~ 0.8 P = (0.8)(1 atm) = 0.83 atm Change in P = 1 - 0.83 = 0.17 atm

Answer 458

Fe(OH)3 -> Fe + 3OH Ksp = [Fe][OH]^3 Ksp = (x)(3x)^3 You would plug in 4x10^-10mol/L for x

Answer 459

Carbon 1 An R group will weakly donate electrons on carbon 3, making an unstable carbanion No such R group on C1

Answer 460

Hydrazine is nucleophile Carbonyl is electrophile Nucleophilic addition to carbonyl C

Answer 461

Acetal Alcohol adds via SN2, would add with its R group (carbon chain)- this would give an acetal (2 -OR groups)

Answer 462

Be least polar MW has little to do with rate at which gas passes through stationary phase first MW only affects elution order to the degree it alters boiling point

Answer 463

Fragments that hit last will have highest mass/charge ratio-> heaviest will hit last CH2Br* will hit last (Also H3Br* could not be a fragment because this would require 2 different fragments being recombined somehow)

Answer 464

Ketones More likely to be attacked by a nucleophile!

Answer 465

Spontaneous dissociation of one protonated alcohol Methyl shift Other alcohols H is abstracted-> carbonyl forms

Answer 466

H2S is a nucleophile Sulfur will attack carbonyl C Oxyanion will be protonated to create water (leaves) Thioketone (R2C=S) formed

Answer 467

3-oxobutanoic acid 4 carbon chain with carboxylic acid on the end, and carbonyl on C3 To do decarboxylation, must be resonance to stabilize carbanion Ketone must be in beta position

Answer 468

Amide- NH bonded to carbonyl (Anhydride- 2 ketones with oxygen in the middle) Amide nitrogen attacks one carbonyl C. Double bond goes up to O then lone pairs fall back down and know off middle O of anhydride. Left with amide

Answer 469

Carboxylic acid OH group attacks carbonyl C Double bond goes up to O, lone pairs fall back down and Cl is knocked off The OH group is still attached and double bond is back on carbonyl C, so get carboxylic acid

Answer 470

ketone on carbon in alpha position relative to carboxyl group

Answer 471

tert-butanol + acid will eliminate alcohol, but no good nucleophile to form ether ethyl alcohol + ethyl tosylate- CORRECT, ethanol is nucleophile, ethyl tosylate is leaving group ethyl alcohol + ethylamine is 2 nucleophiles, no leaving group tert-butanol + tert-butyl Cl is sterically hindered and tert-butyl Cl is poor electrophile

Answer 472

unless you can create 5 degenerate orbitals in 3d (4s1 3d5)

Answer 473

carboxylic acid

Answer 474

s^-1 = first order, | so 2 x (6.5x10^-8) = 1.3x10^-7 is reaction rate

Answer 475

open reaction vessel to atmosphere- combustion gives water and CO2 gas, so opening to atmosphere allows CO2 gas product to be lost--> pushes reaction forward

Answer 476

benzene- conjugated system is more stable -> less energy -> longer wavelength

Answer 477

concentration cell | proton gradient drives charge conduction

Answer 478

``` Galvanic aka voltaic concentration cell (special type of galvanic cell) ``` electrolytic cell is nonspontaneous

Answer 479

current runs from cathode to anode electrons flow from anode to cathode reduction occurs at the cathode (RED CAT)

Answer 480

``` always opposite spontaneous cell (galvanic) has positive emf nonspontaneous cell (electrolytic) has negative emf ``` emf is voltage of cell- positive emf means the cell is able to release energy

Answer 481

electrical potential --> kinetic energy

Answer 482

precipitation process onto cathode itself in galvanic cell. cations of salt bridge flow into solution on cathode side to balance out charge of ions left in solution when cations are reduced and precipitate onto the electrode

Answer 483

half reactions must occur in separate compartments in galvanic cells do not need to be separated in electrolytic cells because the reaction is nonspontaneous- must provide an external source to force the reaction anways

Answer 484

positive- this is an electrolytic cell

Answer 485

F is charge carried by a mole of electrons charge of electron x mole of electrons 1.6x10^-19 x 6.02x10^23 ~ 10^5 C/mol e-

Answer 486

concentration cell therefore have same reduction potential so current is function of concentration gradient

Answer 487

electrolytic cell- external power source reverses electroplating process and concentrates acid solution. reverses cell potential (Emf)

Answer 488

cathode attracts cations | anode attracts anion

Answer 489

galvanic cell- electrode with more positive reduction potential is at cathode reduction occurs at the cathode

Answer 490

in electrolytic cell, species with lower reduction potential is forced to be reduced by external power source Ecell = Ecathode - Eanode reduction always occurs at cathode Ecell = -0.036 - 0.534 = -0.57V (electrolytic cells have negative Emf because Emf is opposite sign of free energy, which is positive for nonspontaenous reaction)

Answer 491

log(>1) is positive log(<1) is negative log(1) = 0 same goes for ln

Answer 492

zinc is reduced Emf = Ecathode - Eanode reduction always occurs at cathode Emf = -0.7 - 0.3 = -1V

Answer 493

NH4NO3 salt bridges contain inert electrolytes, ionic compounds are strong electrolytes SO3 is covalently bonded- will not dissociate in solution

Answer 494

bent (two groups, two lone pairs) tetrahedral (4 groups) trigonal pyramidal (3 groups, 1 lone pair)

Answer 495

SN2 prefers unhindered, strong nucleophile polar protic solvent creates strong H bonds that stabilize nucleophile, inhibit substitution so SN2 prefers polar aprotic

Answer 496

polyurethane pipe if rusting is oxidation process, than the thing least likely to rust will have highest reduction potential (least likely to be oxidized) this option doesn't even have metal in it- unlikely to rust

Answer 497

Cu2+ must be reduced ions in solution must be reduced to Cu(s)

Answer 498

PV=nRT compared to STP, volume is 2x and moles is 3x P will be 3/2 or 1.5x --> 1.5atm total 2 H2O for every 1 CO2, so partial pressure of CO2 will be a third of total... 0.5atm

Answer 499

to compare solubility, take power of Ksp and divide by number of ions formed - 12/4 = -3 - 3/3 = -1 - 3/4 = -0.75 --> Fe(NO2)3 is most soluble because this is the least negative

Answer 500

molality (mol/kg)- mass doesn't change with temperature | solutions expand with temperature- affects molarity

Answer 501

CaSO4 ammonium and nitrate always soluble SO4 not soluble with group 1 elements

Answer 502

``` osmotic pressure = iMRT i = 3 M = 220/110 R = 0.08 T = 298 osmotic pressure = (3)(220)(0.08)(298)/(110) ```

Answer 503

pH > pKa, [HA] more base | pKa of 9.1 in pH of 8--> more acid

Answer 504

diamagnetic- all electrons paired, won't interact with magnetic field paramagnetic- unpaired electrons, will interact with magnetic field

Answer 505

make primary amines with potassium phthalimide (protected form of ammonia) to prevent multiple alkylations (prevented by steric hinderance of phthalimide)--> follows SN2

Answer 506

uses potassium cyanide and an aldehyde to make amino acids

Answer 507

glycine is not chiral, so neither L or D (or S or R) L amino acids- H with dashed line (behind plane) cysteine- only R amino acids

Answer 508

H2SO4 then NaOH amines are weak bases- need strong acid (H2SO4) to be protonated phenols are weak acids- need strong base (NaOH) to be deprotonated

Answer 509

boiling chips create air bubbles that break surface tension of liquid being heated- prevent superheating and bumping

Answer 510

(CO3)^2- + H2O -> HCO3- + OH- | red litmus paper will turn blue in a base

Answer 511

atomic radius decreases from left to right | because effective nuclear charge increases from left to right, drawing in outermost electrons

Answer 512

NO2- + H2O -> NO3 + OH- | NaNO2 is basic

Answer 513

C1 | carbon with -OR

Answer 514

``` methanal = formaldehyde ethanal = acetaldehyde propanal = propionaldehyde (-al = aldehydes) ```

Answer 515

acetone (-one = ketone)

Answer 516

methanoic acid = formic acid ethanoic acid = acetic acid (carboxylic acids)

Answer 517

carboxylic acid derivative | hydroxyl replaced with alkoxy

Answer 518

carboxylic acid derivative | hydroxyl replaced by amino group

Answer 519

angle- bond angles deviate from ideal | torsional- eclipsed or gauche

Answer 520

same molecular formula | type of stereoisomer, but requires breaking/ reforming bonds (enantiomers, diastereomers)

Answer 521

``` dextrorotatory = CW, or (+) levorotatory = CCW, or (-) ```

Answer 522

tosyl/methyl chlorides protect alcohols and other nucleophiles (nucleophile attacks it) diols protect carbonyls

Answer 523

NO. must have odd mass number or else nuclear spin is zeroed out

Answer 524

LiAlH4 is only one strong enough | amide is carboxylic acid derivative with amine group instead of hydroxy group

Answer 525

first ionization energy of Na gives noble gas electron configuration

Answer 526

benzene sp2 = 3 bond regions (double bond, single C bond, H bond) sp3 = 4 bonds (4 single bonds as in carbons of cyclohexane) bond regions can be lone pairs or bond to another atom

Answer 527

all of these are true!

Answer 528

temperature can affect yield by changing Keq!! | enzymes only affect rate!

Answer 529

33% sp = s+p sp2 = s+p+p --> 1/3 is s sp3 = s+p+p+p

Answer 530

double bond counts as one whole ring counts as one triple bond counts as 2

Answer 531

give bonding electrons to most electronegative atom hydroxyl: O starts with 6 valence e, gains all bonding e- so it ends up with 7--> -1 oxidation number H began with 1 and now has 0--> +1

Answer 532

basic- deprotonation (abstract alpha H- most acidic H) | acidic- protonation

Answer 533

Ba(OH)2 and H2SO4--> Ba2+ and SO4^2- will be insoluble

Answer 534

delocalized valence electrons

Answer 535

exist as cations, reduction used to purify metals (reduction of copper cation Cu2+ to produce solid Cu)

Answer 536

physiological- 37*C, 310K room- 25*C, 298K freezing water- 0*C, 273K

Answer 537

nucleophilicity increases going down periodic table due to greater size and polarizability

Answer 538

increase solubility of inorganic compounds into organic solvents

Answer 539

higher oxidation = higher priority | the highest priority group will determine the suffix

Answer 540

normal, as in straight chain alkane

Answer 541

geminal diol (on same carbon)- these spontaneously dehydrate to lose water, producing carbonyl (C=O)

Answer 542

2-propanol

Answer 543

ethyl alcohol

Answer 544

aldehydes formaldehyde = methanal acetaldehyde = ethanal (an acetyl group with just an H attached, in other words!) propionaldehyde = propanal

Answer 545

CH3CO- (carbonyl with methyl on one side)

Answer 546

2-propanone (ketone)

Answer 547

carboxylic acid

Answer 548

carboxylic acids formic acid = methanoic acid acetic acid = ethanoic acid (an acetyl group with a hydroxyl attached, in other words) propionic acid = propanoic acid

Answer 549

esters!! hydroxyl group replaced with alkoxy group (-OR, where R is hydrocarbon)

Answer 550

two carboxylic acids, one water removed | many anhydrides are cyclic because of intramolecular dehydration

Answer 551

``` n = shell l = subshell ml = orbital ```

Answer 552

yes- that's how you get a single bond from a double bond double bonds stronger than single bonds, but pi bond weaker than sigma bond. you just break the pi bond to get the single bond

Answer 553

two p orbitals

Answer 554

sp (bonded to just the two H)

Answer 555

lewis acid = electrophile | lewis base = nucleophile (unless it's too bulky)

Answer 556

coordinate covalent bond- lewis base is source of all electrons

Answer 557

alkane- very weak acid, so strong conjugate base | alcohol and water are fairly strong acids, so weaker conjugate bases

Answer 558

bond strength decreases down periodic table, so acidity increases acidity- right and down is increase (HCl would be bottom right) basicity- up and left is increasing

Answer 559

enol form of carbonyl-containing carbanions is stabilized by resonance, so their H are acidic and easily lost (enol has hydroxyl group and C=C on alpha C)

Answer 560

amides and amines

Answer 561

carbon, hydrogen, oxygen, or nitrogen with a minus sign or lone pair (CHON-)

Answer 562

protic solvents protonate nucleophile or H bond to it

Answer 563

polar protic solvents, nucleophilicity increases down periodic table (normal trend) polar aprotic solvents, nucleophilicity increases UP periodic table (opposite)- relates directly to basicity

Answer 564

nucleophiles

Answer 565

SN1- planar intermediate gives racemic mixture | SN2- backside attack, requires strong nucleophile, inversion of stereochemistry

Answer 566

good oxidizers. oxidation is increase number of bonds to O or other heteroatoms (atoms not C or H)

Answer 567

H2CrO4 KMnO4 H2O2 (oxidizers)

Answer 568

alkene- make carboxylic acid and ketone (split the double bond into two molecules) alkyne- 2 carboxylic acids

Answer 569

vicinal diol

Answer 570

reducing agents- they produce H- ion

Answer 571

aldehydes generally because less steric hinderance

Answer 572

aldehyde gets you acetal ketone gets you ketal (done to protect group)

Answer 573

acid/base- first step is protonate/deprotonate | nucleophile- attacks electrophile and forms bond

Answer 574

remove protecting groups

Answer 575

hexanal (PCC, oxidizer, stops at aldehyde)

Answer 576

1 equivalent of NaHCO3 gives 1 eq of Na+, so Na+ molar concentration is also 0.01mol/L but 1 equivalent of Na2CO3 gives 2 eq of Na+, so Na+ molar concentration is also 0.02mol/L equal volumes of both solutions, so resulting molar concentration will be average (0.01 + 0.02) / 2 = 0.015mol/L of Na+(aq)

Answer 577

Na is +1, (OH)4 is -4, so Al is +3

Answer 578

hydroxyl H of phenols are acidic due to resonance of phenol ring ortho= groups on adjacent carbons meta= groups with one C in between para= opposite side of ring ortho will be most acidic because less separation of charge

Answer 579

phenols because resonance with aromatic ring

Answer 580

aldehydes hydrated to form gem diols, oxidized to carboxylic acids

Answer 581

they're already as oxidized as can be! (without breaking a bond) same reason alkyl chain can't be reduced!

Answer 582

CrO3, strong oxidizer

Answer 583

make better leaving group | protecting groups

Answer 584

Sulfur with 2 double bonded O, 1 negative charged O, 1 methyl group

Answer 585

electrophiles | ubiquinone is e- carrier of complex I, II, and III

Answer 586

acidic workup- deprotection (alcohol was used as protecting group)

Answer 587

trigonal planar (not trigonal pyramidal) because of partial double bond character from neighboring carbonyl

Answer 588

rate constant of forward/reverse rxns | K(f)/K(r)

Answer 589

primary amines

Answer 590

``` if A (central atom) is alkali or alkaline earth metal, compound is basic if A is nonmetal, compound is acidic ``` also: if electronegativity difference between A and O is large, A-O bond breaks and OH- is released if electronegativity of A is large, the O-H bond breaks and releases H+

Answer 591

sucrose- lacks hemiacetal group necessary to undergo mutarotation (ring opening) intermediate of ring opening is aldehyde

Answer 592

radial size of electron cloud- principle quantum number most closely associated with potential energy of the electron, which is proportional to the square of the distance of 2 oppositely charged particles

Answer 593

equal to ratio of weight of object in air to difference of submerged weight and weight in air: object density / fluid density = weight/ (weight - submerged weight)

Answer 594

ratio of distance travelled by analyte/ distance travelled by solvent

Answer 595

would caused decreased solubility of saturated compound, shifting equation left

Answer 596

ester--> anhydride cannot happen higher reactivity can form derivative of lower reactivity, but not other way around through nucleophilic rxn anhydride > esters and carboxylic acids > amides

Answer 597

electron-withdrawing groups increase acidity and therefore decrease stability !!

Answer 598

more alkyl substituents! electron donating, which stabilizes positive charge! (stable = nonreactive)

Answer 599

carbonyl is nucleophile in condensation rxn | carbonyl is electrophile in nucleophilic addition

Answer 600

tetrahedral- pi bond is broken and the pi electrons pushed onto oxygen if a good leaving group is present, the carbonyl will reform (but only if there's a good leaving group)

Answer 601

both! triple bond/ electronegative N makes it acidic | deprotonation makes it nucleophilic

Answer 602

nucleophilic substitution, you get an imine

Answer 603

``` enolate intermediate (negative charge on O, double bond between C=C below), which is resonance stabilized now follow up with acid (protonate) and you have an enol ```

Answer 604

aldehydes, because extra alkyl group of ketone is destabilizing (e- donating) for carbanion (remember, in carbocations alkyl groups are stabilizing, but here deprotonation gives carbanion, so negative charge will destabilize)

Answer 605

alpha H of less substituted alpha C will be removed first because of less steric hinderance (kinetic product), but this is not as stable. favored by rapid, irreversible, low temp, sterically hindered base rxns eventually thermodynamic product will win out (more substituted alpha C). favored by high temp, slow rate, reversible, weaker bases

Answer 606

imine: N=C enamine: C=C

Answer 607

contains ALDehyde and alcohOL aldol condensation: combining 2 ketones/aldehydes because one acts as electrophile (in keto form) while other acts as nucleophile (in enolate form after deprotonation by base)

Answer 608

acetone will be nucleophile after addition of strong base (enolate ion), because benzaldehyde doesn't have an alpha proton to be abstracted (benzene ring with aldehyde group)

Answer 609

ethanal + base = aldol (deprotonates), then acid stops the reaction --> get 3-hydroxybutanal *you're combining 2 ethanals in aldol condensation*

Answer 610

- NH2 and -OCH3 are e-donating | - NO2 and halides are e-withdrawing

Answer 611

secondary and tertiary alcohols cannot be oxidized to carboxylic acids because they already have at least 2 bonds to other carbons

Answer 612

carboxylic acid + ether in acidic conditions (O of carboxylic acid is protonated, enhances polarity of bond and makes carbonyl susceptible to nucleophilic attack) condensation rxn- water is leaving group

Chem and Orgo Flashcards

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