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ochem 1 Flashcards

1
Q

What is stronger a sigma bond or a pi bond? Why?

A

sigma is stronger. allow for electron density to be concentrated to a much larger degree between 2 nuclei. pi bond weaker because the bond is in a higher energy state

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2
Q

the first bond formed between two elements is a __ bond

A

sigma

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3
Q

As the radius of either atom increase, the p orbitals are ___ ___, resulting in less __. leading to a ___ pi bond

A

spread apart, overlap, weaker.

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4
Q

are sigma bonds or pi bonds more reactive?

A

pi bonds

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5
Q

What is hybridization?

A

Atoms, when bonded, hybridize (i.e., mix) their higher and lower energy valence electron orbitals to form “hybrid orbitals” with intermediate energy

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6
Q

How to determine hybridization

A

count number of electron densities and minus 1

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7
Q

What is the percent of s character of the hybrid oxygen orbital in water?

A

sp3, 25% s character

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8
Q

What is the Valence Shell Electron Pair Repulsion Theory?

A

The theory that predicts which shape molecules will take

due to the repulsion of lone pairs of electrons

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9
Q

name the shapes and bond angles of sp, sp2, sp3, sp3d, sp3d2 orbitals

A

sp= Linear [180 ̊]

sp2= Trigonal Planar or Bent [120 ̊]

sp3 = Tetrahedral, Trigonal Pyramidal, or Bent [109.5 ̊]

sp3d=Trigonal Bipyramidal, Seesaw, T-Shaped, or Linear [90 ̊/120 ̊or180 ̊]

sp3d2= Octahedral, Square Pyramidal, or SquarePlanar [90 ̊]

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10
Q

order the types of bonds (single, double, triple) in decreasing bond length

A

single, double, triple

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11
Q

Rank the bonds (single, double, triple) according to increasing stability

A

single, double, triple

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12
Q

Rank the bonds (single, double, triple) according to increasing reactivity.

A

single, triple, double

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13
Q

Rank the bonds (single, double, triple) according to increasing bond strength.

A

single, double, triple

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14
Q

Describe the forces responsible for the strength of a bond. What is the relationship between potential energy and bond length?

A

A chemical bond is a balance of electrostatic forces. We know that species with opposite charges (i.e., nuclei and electrons) will be attracted to each other with a force given by Coulomb’s Law: F = K(qq/r2). However, remember that there are also repulsive forces between the two nuclei and between electrons. The bond is formed at a sort of “sweet spot” where potential energy is lowest. Increasing bond length or decreasing it would raise the energy of the bond and therefore weaken it.

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15
Q

Which atom is the most electronegative?

A

fluorine

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16
Q

Which atom is the least electronegative?

A

francium

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17
Q

How to calculate dipole moment?

A

u= sigma(d)

sigma = charge 
d = distance between charges
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18
Q

molecules with __ or more dipole moments can have NO __ __ when their geometric orientation causes the dipole moments to __ each other out

A

2, net dipole, cancel

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19
Q

energy is always __ when a bond is formed, and ___ when a bond is broken

A

released, required

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20
Q

The less stable the bond, the ___ the heat of combustion

A

greater

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21
Q

the more stable the bond, the ___ the heat of combustion

A

lower

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22
Q

What is a coordinate covalent bond?

A

bond which both electrons shared in the bond are donated by one atom.

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23
Q

What is the octet rule?

A

atoms of low atomic number (<20) tend to gain or lose electrons to obtain exactly 8 electrons in their valence shell

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24
Q

exceptions to octet rule

A

1) Hydrogen and Helium: Stable with only two electrons in their valence shells (e.g., H2)
2) Boron and Beryllium: Stable with only six electrons in their valence shells (e.g., BF3)
3) Atoms from the third period or higher can accept more than eight electrons. Common MCAT examples include: PCl5, SF6, PO43- and SO42-.

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25
What is formal charge?
The difference between the # of electrons in an atom’s valence shell when it is in its ground state and the number assigned to it in a molecule.
26
equation for formal charge
formal charge = valence - assigned
27
regarding resonance, the actual structure ___ resonate back and forth between forms, it is a ___ weighted hybrid of the contributing structures
does NOT, permanent
28
Drawing resonance structures rules
Atoms can never be moved. Single bonds can never be moved. All structures must obey the octet rule All structures must have the same number of total valence electrons The tail of an arrow showing electron flow during resonance can only start from a lone pair, a double, or a triple bond
29
ranking resonance structures rules
1. allows the most atoms to have a full octet 2. has least formal charge 3. places formal charge on most electronegative atom
30
more stable species, has more __-
resonance
31
What is Huckel's Rule?
To exhibit aromaticity, a ring system must have exactly 4n + 2 pi electrons
32
What does alkoxy look like?
- O--R
33
acetyl group
Ch3-C=O
34
What are isomers?
Two molecules are isomers if they have the same molecular formula but are actually different compounds.
35
How to calculate the maximum number of optically active stereoisomers
2^n | n= chiral centers
36
What is a structural isomer
Same formula, different bond-to-bond connectivity
37
what are Stereoisomers
Same formula, same bond-to-bond connectivity, but different in the 3-D arrangement of their substituents. There are two categories of stereoisomers: enantiomers and diastereomers
38
what is Relative Configuration
Two molecules have the same relative configuration if their spatial arrangement is identical, but they have one—and only one—non-identical substituent
39
what is observed rotation
the degree to which a sample rotates plane polarized light
40
What is specific rotation?
dividing observed rotation by the length of the tube and the concentration. Specific rotation could therefore be described as “observed rotation per length, per concentration unit.”
41
What is a polarimeter?
apparatus that measures the rotation of plane-polarized light as it passes through a sample
42
What is plane polarized light?
light that exists in only a single plane
43
What does optically active and inactive mean?
active - substance does rotate plane-polarized light | inactive- doesn't
44
what is a racemic mixture?
50/50 mix of the two absolute configurations of a compound (R and S)
45
If a compound rotates light clockwise it is ___
+ or d (dextrorotary)
46
If a compound rotates light counter clockwise ____
(-) or l (levorotary)
47
What are diastereomers?
Two molecules with the same formula and the same bond-to-bond connectivity that are non-identical, but are NOT mirror images.
48
What are geometric isomers?
(cis/trans): cis = same side; trans = opposite sides. The E/Z Convention: prioritize the two constituents on each carbon by molecular weight (as you do for R/S). If the two higher priority substituents are on the same side = Z. If the two higher priority substituents are on opposite sides = E
49
cis isomers often have a __ __, but trans do NOT
dipole moment
50
What are epimers and anomers?
epimers- Diastereomers that differ at only one chiral center. Many pairs of carboydrates are epimers (e.g., glucose and galactose). anomers - Molecules that differ only in their spatial orientation at the anomeric carbon of a ring structure. If the anomeric OH/OR group and the CH2OH group are on the same side of the ring = Beta, if they are on the opposite side = Alpha.
51
What are meso compounds?
molecules w 2 or more chiral centers that contain a plane of symmetry. This symmetry cancels out their optical activity
52
nucleophiles always attack ___
electrophiles
53
a strong base favors the ___ in acid/base equilibrium
conjugate acid
54
nucleophilicity is a function of ___
kinetics - how easily a molecule will react , nothing about how stable the new bond will be
55
electrophiles are ___ species with a full or partial __ charge
electron poor, positive
56
What are leaving groups?
atoms or molecules that leave the parent molecule during a reaction and take both electrons from the bond w them.
57
what are the steps of E1
1) The dissociation of the leaving group, resulting in formation of a carbocation [slow step]. 2) The abstraction of a proton with collapse of the electrons to form a double bond (which quenches the carbocation) [fast step].
58
What are the steps for E2?
1) The single-step abstraction of a proton with collapse of the electrons to form a double bond and ejection of the leaving group.
59
What are the steps in SN1?
1) The dissociation of the leaving group, resulting in formation of a carbocation [slow step]. 2) Attack of the carbocation by the nucleophile [fast step].
60
What are the steps for SN2?
1) The single-step “back side attack” of the electrophile with simultaneous ejection of the leaving group.
61
E1 is __ order and is favored by ___
first; weak bases, tertiary carbons only, polar protic solvents
62
SN1 is a ___ order reaction, it is favored by ___
first; poor nucleophiles, tertiary carbons, polar protic solvents
63
E2 is a ___ reaction, and is favored by ____
second, strong and/or bulky bases
64
SN2 is a ___ order reaction, it's favored by ___
second; good nucleophiles, methyl, primary or secondary carbons (inversion)
65
What are alkanes?
Compounds made entirely of carbon-carbon or carbon-hydrogen single bonds (e.g., gasoline, tar, crude oil, butane, methane, etc.)
66
alkanes are ___ in water, ___ density, and have what kind of polarity?
insoluble, low, non-polar
67
boiling pt increases with ___ chain length
increasing
68
boiling pt decreases with __ branching
increased
69
melting point increases with ___ chain length and/or molecular weight
increasing
70
___ alkanes have the highest melting points. Among branched alkanes, __ branching increases melting point
straight-chain, increased
71
What is ring strain regarding cyclic compounds?
cycloalkanes create ring strain because they force bond angles to deviate from the optimum tetrahedral angle of 109.5°
72
bicyclic ring systems generally exhibit __ ring strain than do monocyclic rings
more
73
are large substituents more stable at the equatorial or axial position?
equatorial
74
rings near __ to __ members or above will have ring strain equal to that of cyclohexane
10-12
75
How are radicals formed?
homolytic cleavage sends one electron to one species and one to another
76
How to make a alkane from an alkene
CH2=CH2 + H2/Pd(catalyst) → CH3CH3 | syn addition
77
What is more stable? A tri-substituted alkene or a di-substituted alkene?
trisubstituted
78
What is the difference between a phenyl and benzyl? What is the molecular formula for a benzene?
phenyl - benzene directly attached to primary chain benzyl- a CH2 is attached to the primary chain on one side and benzene on the other C6H5
79
Alcohol can behave as a __ or a ___
nucleophile, lewis acid
80
For alcohols, increasing molecular weight ___ boiling pt, boiling pt decreases when branching ___
increases, increases
81
melting pts of alcohols go up when polarity and H-bonding ___
increases
82
hydrogen bonding can occur with what atoms?
F, O, N
83
Why are most alcohols highly soluble in water?
alcohol can hydrogen bond with water
84
alcohol acidity increases from __ to __ to __
tertiary, secondary, primary
85
formation of an alkyl halide from an alcohol via SN2
CH3OH + HCl → CH3OH2+ + Cl- → CH3Cl + H2O
86
formation of an alkyl halide from an alcohol via SN1
Via SN1: R3COH + HCl → R3COH2+ + Cl- → R3C+ + H2O → R3CCl
87
What are the common oxidizing agents for alcohols
O3, Cr2O7, CrO4, KMnO4, Jones, Collins, PCC, PDC
88
primary alcohols can be oxidized to __ and __
aldehydes and carboxylic acids
89
secondary alcohols can be oxidized to __
ketones
90
tertiary alcohols can be oxidized to __
cannot be oxidized further
91
What are common reducing agents?
NaBH4, LiAlH4 and H2
92
NaBH4 can reduce __ and __
aldehydes and ketones
93
LiAlH4 and H2/pressure can reduce __
aldehydes, ketones, carboxylic acids and esters
94
LiAlH4 produces __ equivalents of hydride ions and NaBH4 produces __ equivalents
2, 1
95
What is the pinacol rearrangement?
vic-diol + hot acid → ketone or aldehyde
96
How to protect alcohols
Protection with TMS: ROH + TMS → RO-Si(CH3)3 • Protection by MOM (Mothers are very protective! MOM stands for methoxymethyl ether): ROH + Base → RO- + CH3OCH2Cl (MOMCl) → ROCH2OCH3 (RO-MOM) • Acidification will remove either protecting group to restore the alcohol.
97
reaction with SOCl2 and PBr3
o ROH + SOCl2 → RCl | o ROH + PBr3 →RBr
98
What are the steps to form a tosylate or mesylate?
1) The alcohol attacks the tosyl or mesyl halide via SN2, kicking off a halide ion. 2) A hydrogen is abstracted by the halide ion, quenching the charge on the oxygen.
99
Why would we want to form a tosylate or mesylate?
they are good leaving groups that readily react with almost any nucleophile
100
name the steps of the dehydration of an alcohol to an alkene
1) The alcohol is protonated by the acid 2) The “good leaving group water” leaves, forming a carbocation 3) Methyl or hydride shifts can occur, but only if it results in a more stable carbocation. 4) A water molecule abstracts a proton and the electrons collapse to quench the carbocation and form an alkene.
101
the alkene is favored by __, __ acid ; the alcohol is favored by __, __ acid
hot, concentrated | cold, dilute
102
What is the purpose grignard synthesis?
Production of an alcohol with extension of the carbon chain
103
What are the steps of a Grignard reaction?
1) Due to the very low electronegativity of Mg, the R group in RMgBr gains significant electron density and more or less acts as if it were a carbanion (R:-), attacking the electrophilic carbonyl carbon. This occurs in a single step, kicking the electrons in the C=O bond up onto the oxygen. 2) The negatively charged oxygen is protonated, yielding an alcohol.
104
What is an ether?
An ether is an oxygen bonded to two –R groups (R-O-R)
105
What are some properties of ethers?
o Very non-reactive o Weakly polar o With short –R groups ethers are slightly soluble in water o Most non-polar species are soluble in ethers o Low boiling point (no H-bonding)
106
ethers are excellent __
solvents
107
What is an epoxide?
Epoxides are cyclic ethers involving one oxygen and two carbons in a three-member ring.
108
How to open an epoxide
Epoxide rings can open via either an SN2 mechanism with good nucleophiles, or an “SN1-like” reaction with poor nucleophiles. In SN2 reactions the good nucleophile attacks the least substituted epoxide carbon and in SN1-like reactions the nucleophile attacks the carbocation formed on the most substituted epoxide carbon.
109
the greater the difference in the __ of two atoms in a bond, the more polar the bond
electronegativity
110
How to determine if a group is electron donating or withdrawing
1) Look at the first atom from the point of attachment. Compare its electronegativity to the atoms bound to it. If it is more electronegative, it will bear a partial negative charge and if it is less electronegative, it will bear a partial positive charge. 2) Atoms with full or partial positive charges withdraw from whatever they are attached to. Atoms with full or partial negative charges donate to whatever they are attached to. 3) Hydrogen is considered neither electron donating nor withdrawing. 4) Alkenes are weakly electron withdrawing (just memorize this one).
111
Label each of the following as electron donating or electron withdrawing: alkyl groups, nitro groups, cyano groups (a.k.a. nitriles), sulphones, amines, carboxylic acids, esters, alcohols and quaternary amines.
``` Alkyl - weakly electron donating nitro - strong withdrawing groups cyano - electron withdrawing sulphones - electron withdrawing amines - electron donating carboxylic acids - electron withdrawing esters - electron withdrawing (assuming connection to the carbonyl; if connected to the oxygen of the –OR group, an ester is electron donating); alcohols are electron donating; quaternary amines are strongly electron withdrawing. ```
112
What to look for when ranking acidity
look at stability of the conjugate base, resonance stabilization
113
How to rank basicity
Electron donating groups increase basicity, while electron withdrawing groups decrease basicity.
114
steric hindrance favors __ over ___
basicity, nucleophilicity
115
reactivity favors __ over __
basicity, nucleophilicity

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