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Ochem 1 Flashcards

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1
Q

Hydrazine

A

N2H4

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2
Q

Why are alcohols soluble in water?

A

They can H bond with water

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3
Q

Cycloalkanes and ring strain

  • How much ring strain do big, small, bicyclic & monocyclic cycloalkanes have?
A
  1. Cycloalkanes w/ LESS than 6 C’s have increasingly more ring strain
  2. Really BIG (10+) rings have enough freedom to approximate 109.5º
  3. BICYCLICring systems haveMOREring strain thanMONOcyclic rings
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4
Q

1º,2º,3º OH groups have 1,2, and 3 ___ ___ which do what to charge?

What does this mean?

A

Have 1,2, and 3 donating groups to destabilize charge

this is why 3º is less acidic than 1º

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5
Q

Hückel’s Rule (for aromaticity)

to exhibit aromaticity

a ring must have EXACTLY __+__ electrons

A

to exhibit aromaticity

a ring must have EXACTLY: 4n+2π electrons

​From what I’ve gathered, “n” is just 1 (at least it is for benzene…( 4(1) + 2π= 6 )

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6
Q

Hemiketal

A
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7
Q

Alkenes are _____s!

Why?

A

Nucleophiles!

  • π bonds are e’ dense and will attach E:philes
    • forming a new bond to one of the C’s
    • and leaving a CCI on the other
      • CCI then attacked by a Nu:
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8
Q

What does an SN2 rxn look like?

A
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9
Q

Rank BOND REACTIVITY for:

  • Single bonds
  • Double bonds
  • Triple bonds
A

triple>double>single

more reactive bc of π bonds

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10
Q

3º ROHs can only be oxidized into ___?

A

PSYCHE!

They cant be oxidized at all!

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11
Q

1º ROH can be oxidized into?

A

1º ROH⇒Aldehydes⇒Carboxylic Acids

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12
Q

Alcohols are less/more acidic than water

  • Rank alcohol acidity
A

LESS acidic than water

  • ROH acidity increases from:
    • (most acidic) 1>2>3 (least acidic)
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13
Q

Imine

A
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14
Q

Hybridization:

sp3, 1 LP

A

Trigonal Planar

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15
Q

Hybridization:

sp3d, 2 LPs

A

T-shaped

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16
Q

What is a racemic mixture a mixture OF?

A

50/50 mix of R and S enantiomers

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17
Q

Anomers

  • If anomeric OH/OR group and CH2OH group are on opposite sides of the ring, what kind of anomer is it?
A

ALPHA anomer

on the “Alpha-site side”

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18
Q

Alcohols behave as either: ___s or as a ___

A

1) Nucleophiles
* (the lone pair on oxygen acts as a Lewis base)
2) Lewis acids

  • ..when they are oxidized to carbonyl groups
    • the oxygen ACCEPTS A PAIR OF ELECTRONS (Lewis Acid) from the O-H bond as the proton is abstracted
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19
Q

Hybridization:

sp3d2, 1 LP

A

Square Pyramidal

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20
Q

Are Alkyl substituents strong or weak e’ donating groups?

A

weak

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21
Q

Absolute conformation (__ & __)how do you assign priority to 4 R groups?

A

Assign priority starting with:

HIGHEST MW

(heavier=higher priority, i.e. 4)

(lighter, like H=lower priority, i.e.1)

If 1–>3 is clockwise=R

If 1–>3 is counter clockwise =S

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22
Q

Gringard Synthesis:

Describe the 2 steps (using R-MgBr)

A

1) Mg has VERY LOW ELECTRONEGATIVITY

  • so the R group in R-MgBr attacks the electrophilic carbonyl C
  • Occurs in single step
    • kicking e’s in C=O bond onto the oxygen

2) (-) charged oxygen is protonated
* yielding an alcohol

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23
Q

What are diastereomers?

A

Have same MF & connectivity (like steroisomers)

  • are NON-identical, NON-superimposable*
  • mirror images*
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24
Q

Amine

A
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25
Q

RANKING resonance structures

  • ​You want MORE ____s, LESS _____
  • The most STABLE species has the most WHAT?
A

MORE bonds, LESS charges

The most stable species has the MOST POSSIBLE RESONANCE STRUCTURES

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26
Q

Describe the 2-step formation of:

  • TOSYLATES / MESYLATES
A
  1. ROH attacks X (via SN2)
    • kicks off X
  2. H is abstracted by X ion

Mesylates and Tosylates are desirable because they make very good LGs that will react readily with almost any nucleophile

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27
Q

Define “LEVOROROTARY”

  • Using FISCHER PROJECTIONS, differentiate b/t D- Glyceraldehyde and L-Glyceraldehyde
A

compound rotates light

counter-clockwise (-)

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28
Q

2 molecules have the same RELATIVE CONFIGURATION if:

  • Their 3D arrangement is ___, but they have 1 (and ONLY 1) ___-____ _____
A

SAME RELATIVE CONFIGURATION if:

Their 3D arrangement is IDENTICAL, but they have 1 (and ONLY 1) NON-IDENTICAL SUBSTITUENT

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29
Q

Hybridization:

sp3, no LPs

A

TETRAHEDRAL

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30
Q

Structural/ Constitutional Isomers have the SAME____, but different _____

A

Same MF

BUT

Different connectivity

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31
Q

Acetyl

A
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32
Q

ETHERS, ROR’, are excellent…?

A

Solvents!

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33
Q

2º ROHs can ONLY be oxidized into ___

Can they be oxidized any further, like 1° ROHs?

A

Ketones

Can NOT be further oxidized

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34
Q

What are the 2 types of reactions you’ll

see ETHERS, ROR’, used in?

A
  1. Ethers will almost ALWAYS be the SOLVENT
    • ∴ wont participate in rxn
  2. If Ethers DO react, it’ll only be after the O- is protonated by a strong acid (HCl)
    • resulting in a carbocation intermediate
    • which would then be attacked by a nucleophile
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35
Q

Nitrile

A
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36
Q

Ester

HINT: Ester drinks COORS

A
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37
Q

What are a few common OXIDIZING AGENTS?

HINT: OKPeePee!

A
  • O3Cr2O7
  • KMnO4
  • PCC
  • PDC
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38
Q

List 4 characteristics of π bonds

A
  1. prevent rotation
  2. weaker than sigma bonds
  3. less stable
  4. more reactive
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39
Q

Rank bond STABILITY for:

  • Single Bonds
  • Double Bonds
  • Triple Bonds

​Explain what makes the least stable one the least stable

A

single>double>triple

  • Triple bond is LESS stable because it has 2 reactive π bonds!
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40
Q

Aldehyde

A
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41
Q

In DEHYDRATION of an ROH:

  • What is favored by a HOT, concentrated acid?
  • What is favored by a COLD, dilute acid?

In a dehydration reaction, what is the MAJOR product?

A

Alkene

  • is favored by a hot, concentrated acid

Alcohol

  • is favored by a cold, dilute acid

Major** product is the **more substituted

(more stable) alkene

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42
Q

Describe SN2 rxns

A

Rate depends on [] of 2 species

  • so its SECOND order
  • ONE step

STEP:

  • Backside attack of Nu:
    • w/ simultaneous ejection of LG
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43
Q

Carboxylic acid

A

COOH

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44
Q

Alkyl group

A

Hydrocarbons ONLY!!!

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45
Q

Define a “Base” in an ochem reaction

  • What do they do to protons?
  • Are they electron dense or deficient?
  • What kind of charge do they have?
A

ABSTRACT protons

  • are electron DENSE
  • have full or partial (-) charge
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46
Q

Dehydration of ROH: synthesis of an ___.this is an ___ rxn

A

alkeneis an equilibrium rxn

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47
Q

What are Meso cpds?Why dont they have optical activity?Are they diastereomers? Why/Why not?

A
  • -have 2+ chiral centers AND a plane of symmetry
  • POS cancels out optical activity
  • ARENT diastereomers, b/c diastereomers are PAIRS of cpds.
  • Meso cpds are single cpds with a POS-
    • Therefore, can’t be diastereomers NOR enantiomers
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48
Q

Define “ALIPHATIC”

  • If something has a benzene ring, is it aliphatic or not?
A

Relating to organic compounds whose carbon atoms are linked in open chains

  • either straight or branched

rather than containing a benzene ring

Something is either ALIPHATIC or AROMATIC

Example:

Alkanes, alkenes, and alkynes are aliphatic compounds

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49
Q

Enamine

A

“Enamine” is derived from:

  • the affix en-
    • used as the suffix of alkene
  • the root amine
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50
Q

Dehydration of an ROH:

  • Describe the 3 steps
  • What can occur during this reaction?
    • In what circumstance would it occur?
A

Steps:

  1. Protonation of alcohol
  2. Water (which is the LG here) leaves
    • CCI is formed
  3. H2O molecule abstracts proton
    • ​​e’s collapse
      • and form a double bond

Methyl or hydride shifts can occur

if a more substituted CCI is available

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51
Q

What is “anti” addition?

A

Where bonds are formed on OPPOSITE sides (of a metal catalyst, for example)

  • Remember:*
  • Syn=Gay (same sex/sides; is a SIN)*
  • Anti=Hetero (opposite sex/ sides)*
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52
Q

List 4 characteristics of sigma bonds

A

1) DO allow rotation2) stronger than pi bonds3) more stable4) less reactive

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53
Q

What are Enantiomers?

What do they need to have in order to qualify as enantiomers?

A

non-superimposable mirror images

of each other

  • Compound needs to have at least 1 chiral center
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54
Q

Substitution of EPOXIDES can occur via what mechanism?

A

SN1 _or_ SN2

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55
Q

Describe E2 reactions

A

Rate depends on [] of two species

so its a SECOND order, one step reaction

STEP:

  1. Abstraction of H+ leads to double bond formation
    • …while simultaneously ejecting LG
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56
Q

Hybridization:

sp3, 2 LPs

A

Bent (V-shaped)

Ex: H2O

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57
Q

What does it mean when two things are “GEMINAL?”

A

Both bonded to the same Carbon

(are gemelos–twins)

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58
Q

Describe “NUCLEOPHILES”

  • How do they react with atoms around them?
  • Are electron dense/deficient?
  • What’s their charge like?
A
  1. Attack C’s
    • or other central atoms
  2. Are electron DENSE
    • just like bases
  3. Have a full or partial (-) charge
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59
Q

Ketone

A
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60
Q

Acetal

A
61
Q

Gringard Synthesis

  • What is it?
  • What does it result in?
  • What 3 reactants can it use?
A
  • Production of an ROH

…with an EXTENSION (!!) of the C chain

  • Results in increase in the number of C’s
  • Can occur with the following reactants:
    • RMgBr (Main one)
    • Electrophilic DOUBLE BONDS
    • Cyano groups
62
Q

What is it that determines a molecule’s shape

and bond angle(s)?

A

Its Hybridization

sp vs sp2 vs sp3 etc.

63
Q

Define “Stereoisomers”

list the 2 types

A

Same MF, same connectivity

….but different 3D arrangement

2 Types:

  • Enantiomers & Diastereomers
64
Q

Acyl group

A
65
Q

When an alkene is 1 C away from another atom, the ___ ___s are electron ___

A

the π bonds are e’ withdrawing

66
Q

Compare boiling points:

  • cis vs trans isomers
A

CIS > trans

  • b/c of dipole moment, there are increased IMFs in CIS
  • In TRANS, the dipoles cancel
    • which means you’ll have less IMF’s
67
Q

Describe the 5 IUPAC rules for naming a compound

A
  1. Find the LONGEST C chain
  2. The terminal C closest to a substituent is #1
    • if it’s a tie, one w/ next closest subst. is #1
  3. Order groups alphabetically
    • give # to match C to which it is attached
  4. Dont forget di, tri, tetra, etc if multiple copies of the same R group are present
  5. Put hyphens before and after R group #s
68
Q

Mesyl group

A
69
Q

Hybridization (there’s 3 possibilities for this one) and bond angle:

sp3d2

A

90º

  1. Octahedral
  2. Square pyramidal (1 LP)
  3. Square planar (2 LP)
70
Q

Amide

A
71
Q

Hybridization:

sp2, 1 LP

A

Bent (V-shaped)

Ex: SO2, O3

72
Q

Alcohols:

  • _,_,_ bonded to an H can act as H-bond donors/ acceptors?
  • What if they have LPs NOT attached to an H?
A
  • F,O,N can act as BOTH an H bond donor OR acceptor
  • F,O,N atoms w/ LPs that are NOT attached to a H
    • …can only act as H bond acceptors
73
Q

sp hybridization

A

always linear (180º)

74
Q

Ketal

A
75
Q

Dextrorotary

A

cpd rotates light clockwise (+)

76
Q

Protection of Alcohols: what 2 things protect alcohols? What do they protect them from?what thing will remove a protecting group?

A
  • TMS and MOM
  • protect OH from oxidation (or related rxn) while at the same time letting the rxn proceed
  • acidification will remote EITHER protecting group and restore ROH
77
Q

Synthesis of an alkane

A

-reduce an alkene with H2 in presence of a metal catalyst (syn addition, remember?)

78
Q

Anomers:if anomeric OH/OR group and CH2OH group are on the same side of the ring, what kind of anomer is it?

A

ß anomer

79
Q

Hybridization:

sp3d, 3 LPs

A

Linear

ex: XeF2

80
Q

Vicinal

A
81
Q

Physical properties of Ethers

A
  • VERY non-reactive
  • weakly polar
  • ones with short R groups are slightly water soluble
  • most non-polar species are soluble in ethers
  • have low BP (no H bonding)
  • Ethers are excellent SOLVENTS!
82
Q

Formation of an RX from an ROH: -what mechanism is it?-what makes it unique?

A
  • SN2 rxn
  • SN2 are usually one step, but alcohols need to get protonated first
83
Q

___ ___ alkanes have the highest BP. Why?

A

-straight chain-always has higher MP than branched alkanes-among branched alkanes, increased branching=increased MP

84
Q

Nucleophilicity is a function of ____?What does this mean?

A

-is a function of Kinetics-means it quantifies the rate at which a molecule reacts with an E:-describes how easily a molecule will react, but nothing about how stable the new bond will be

85
Q

HYbridization:

sp3d, no LPs

A

Trigonal BIpyramidal

Ex: PF5

86
Q

What are some common reducing agents?Reducing agents reduce a ___ to a __

A
  • NaBH4
  • LiAlH4
  • H2/pressure

…reduce a carbonyl to an alcohol

87
Q

What is specific rotation of a sample?(hint: is ___ per___, per___)

A
  • “is observed rotation per length, per concentration unit”
  • divides observed rotation by length of tube and []
88
Q

Why is cyclohexane more stable than cyclopropane?

A

Cyclopropane has tons of RING STRAIN!

89
Q

Tosyl

A
90
Q

NaBH4 can only reduce ___,___ ONLY

A

aldehydes and ketones only

91
Q

Ether nomenclature

A
  • You can name each R group separately
  • IUPAC wants you to name the LONGER of the 2 R groups as the “parent” chain, and the other R group as a substituent w/ “-oxy” suffix added
    • ex: 1-ethoxyheptane
92
Q

Which cyclic alkane is the most stable? How much ring strain does it have?

A
  • cyclohexane
  • has 0 ring strain
93
Q

Alkynes are nearly identical to ___s in ___?

A

nearly identical to alkenes in how they react

94
Q

Remember the following about enantiomers (3)

A
  1. they have R/S configurations at EVERY chiral center
  2. They rotate PPL to the same degree, but in different directions
  3. They have identical physical properties (BP, reactivity, etc) except for how they rotate PPL and the products they form when reacted with another chiral cpd
95
Q

Hybridization:

sp2, no LPs

A

Trigonal Planar

Ex: BF3

96
Q

What does Valence Shell Electron Repulsion Theory predict?

A
  • predicts shape molecules take due to the repulsion of the LP’s of electrons
    • ex: sp3 can be trigonal bipyramidal, seesaw, t-shaped, or linear depending on amount of LPs
97
Q

Hybridization:

sp3d2, no LPs

A
98
Q

What are E:’s?

A
  • e’ poor species with a full or partial (+) charge
  • accept e’s from either Nu:’s or bases
99
Q

What is a polarimeter?

A

measures rotation of PPL as it passes through a sample

100
Q

Hemiacetal

A
101
Q

Sulfone

A
102
Q

Epoxide

A
103
Q

Basicity is a function of ____. What does this mean?

A
  • of Thermodynamics
  • basicity says nothing about how FAST a rxn will occur
    • Only shows how much the molecule “wants” to react (how stable it is)
104
Q

Alcohol MP properties

A
  • increased MP with:
    • increased Polarity and H-bonding
105
Q

Benzyl

A
106
Q

Describe SN1 rxns

A
  • Rate depends on [] of one species, so its FIRST order-two steps
    1. LG leaves, forms CCI (slow step)
    2. Nu: attacks CCI (fast step)
107
Q

Epoxides suffer from SEVERE what?What does this mean?

A
  • Ring strain!
  • This means they are highly reactive
108
Q

Anhydride

A
109
Q

Conformational Isomers

A
  • AREN’T really isomers!
  • when a molecule rotates around its bonds, these are “conformers,” not isomers
    • think about Newman projections, staggered & eclipsed, etc.
110
Q

Nitro (FG)

A
111
Q

Ether

A
112
Q

Compare melting points: cis vs trans isomers

A

TRANS>CIS

113
Q

What are Epimers?What are a common example?

A
  • A type of diastereomer
  • differ are only 1 chiral center
  • many carbohydrates are epimers
114
Q

Epoxides are ___ ___ involving what?

A

cyclic ethers with 1 O and 2 Cs in a 3-membered ring

115
Q

Cyclic rings create ___ ___ and make bond angles do what?

A
  • ring strain
  • make bond angles deviate from preferred 109.5º
116
Q

What should you know about Radicals? (2)

A
  1. Its HETEROLYTIC cleavage sends ONE e’ to one species and ONE to the other
  2. can also form as damage to the molecule itself (radiation exposure)
117
Q

Physical properties of alkanes

  • Soluble/Insoluble in water?
  • Low/High density?
  • polar/non-polar?
  • What increases BP?
  • What decreases it?
  • What increases MP?
A
  • insoluble in water
  • very low density
  • non-polar
  • BP increases with increasing chain length and/or MW
  • BP decreases with increased branching (decreased symmetry)
  • MP increases with increasing chain length and/or MW
118
Q

Aryl

A
119
Q

What is stronger, a sigma or a π bond?

A

sigma

120
Q

Geometric Isomers: what are they when there’s only 2 R groups attached? What about when there’s more than 2?

A

2 groups: cis (same side), trans (opposite side)2+ groups: E (epposite side), Z (ze zame zide)(prioritize by MW)

121
Q

Remember the following about cis & trans isomers (2)

A
  1. Cis isomers often have dipole moments, but trans DONT (they cancel)
  2. Cis isomers often experience steric hindrance, but trans DONT
122
Q

Carbonyl

A
123
Q

If you see C6H5, what is it?

A

a BENZENE!

  • not a straight chain
  • since it has π bonds, it is unsaturated
124
Q

Hydroxyl

A
125
Q

To be chiral, an atom has to be attached to…?What if it isn’t?

A
  • to 4 DIFFERENT R groups
  • if it isnt, its not chiral
    • therefore not an enantiomer
126
Q

Hybridization:

sp3d2, 2 LPs

A
127
Q

The Pinacol Rearrangement (“vicinal”)-what does the rxn look like?-3 other details

A
  • vicinal diol+hot acid–>ketone or aldehyde
  • the two OH groups must be in vicinal position and C’s bearing them must be tri- or tetra- substituted by R groups
    • if tri-substituted, yields an aldehyde
    • if tetra-substituted, yields ketone
128
Q

What are Leaving Groups?What are the “best” LGs?

A
  • they leave the parent molecule during a rxn and take BOTH e’s from the bond with them
  • Best LG’s are the most stable after they leave
    • (ex: Halides)
129
Q

Alkene stability

A

More R groups=more stable3>2>1

130
Q

Alkoxy

A
131
Q

sp3d bond angle and hybridization (4)

A
  • 90º/120º or 180º (for linear)
  1. trigonal bipyramidal
  2. seesaw (1LP)
  3. t-shaped (2LP)
  4. linear (3LP)
132
Q

sp3 bond angle and hybridization (3)

A
  • 109.5º
  1. tetrahedral
  2. trigonal pyramidal (1LP)
  3. bent (2LP)
133
Q

What is plane polarized light?What is “optically active?”

A
  • Light that exists in only a single plane
  • “optically active”= DOES rotate PPL
134
Q

How do you find the max # of (optically active) stereoisomers?

A
  • =2n
  • “n”=# of chiral centers
135
Q

What catalyzes epoxide rxns, and how?

A
  • Strong acids
    • By protonating O and making it a better LG
136
Q

Describe E1 rxns

A
  1. Depends on [] of ONE species, so its first order
  2. Two-steps:
    1. LG leaves, forms CCI (slow step)
    2. Proton abstraction leads to double bond formation (fast step)
137
Q

sp2 hybridization (2) and bond angle

A
  • 120º
  1. trigonal planar
  2. bent (1LP)
138
Q

Alcohol BP properties

A
  • increased BP with increased MW
  • decreased BP with increased BP
139
Q

Combustion of an alkane is a ___, ___thermic reaction with a ___ Ea

A
  • radical, exothermic rxn with a High Ea
140
Q

What are Anomers?

A
  • a type of diastereomer
  • differ in 3D orientation ONLY at the anomeric carbon (1’) of a ring structure
141
Q

Hybridization:

sp3d, 1 LP

A
142
Q

What are the 3 steps of a radical reaction?

A
  1. initiation
  2. propagation
  3. termination
143
Q

Which step of a radical rxn produces the most product?

A

propagation

144
Q

PEROXIDES

A

RO-OR

145
Q

HYDROGEN PEROXIDE

A

H2O2

146
Q

Hückel’s Rule (for aromaticity)

  • Why is benzene aromatic and the 8-membered ring NOT?
A

4n+2π

  • “n” is just any interger. But it needs to equal the amount of carbons!
  • Benzene: here, “n”=1
    • ​4(1)+2π=6
  • ​For the 8 membered ring, neither n=1 nor n=2 works!
  • You can’t get 8 from either option
    • therefore it isnt aromatic
147
Q

Define observed rotation of a molecule

  • What determines it?
A

degree to which a sample rotates PPL

  • determined by:
    • []
    • length of tube, etc.
148
Q

Vinyl

A

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