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MCAT > Organic Chemistry 1 > Flashcards

Organic Chemistry 1 Flashcards

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MCAT flashcards
1
Q

sp2

A

trigonal planar or bent

120°

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2
Q

sp3

A

tetrahedral, trigonal pyramidal, bent

109.5°

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3
Q

sp3d

A

trigonal bipyramidal, seesaw, t-shaped, linear

90°/120° or 180°

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4
Q

sp3d2

A

octahedral, square pyramidal, square planar

90°

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5
Q

octet rule exceptions

A

hydrogen and helium: stable with 2 e- in valence shell

boron and beryllium: stable with 6 e- in valence shell

atoms from third period or higher can accept more than 8 e-

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6
Q

amine

A
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7
Q

aldehyde

A
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8
Q

alkoxy

A
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9
Q

gem/vic

A
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10
Q

mesyl/tosyl

A
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11
Q

amide

A
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12
Q

anhydride

A
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13
Q

aryl

A
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14
Q

benzyl

A
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15
Q

hydrazine

A
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16
Q

vinyl

A
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17
Q

allyl

A
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18
Q

nitrile

A
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19
Q

epoxide

A
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20
Q

enamine/imine

A
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21
Q

acyl

A
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22
Q

sulphone

A
23
Q

nitro

A
24
Q

acetal/ketal

hemiacetal/hemiketal

A
25
Q

conformational isomers

A

differ by rotation around a single bond

*** not true isomers

26
Q

structural isomers

A

same formula, different bond-bond connectivity

27
Q

enantiomer

A

same bond-bond connectivity, non-identical, non-superimposable mirror images

contain at least one chiral center

1) have opposite R/S configuration at every chiral center
2) rotate plane-polarized light to same degree, but in different directions
3) have all same physical properties except for:
a. how they rotate plane polarized light
b. the products they form when reacted with another chiral compound

28
Q

diastereomers

A

same bond-bond connectivity, non-identical, not mirror images

  • geometric isomers
  • epimers
  • anomers
29
Q

geometric isomers

A

diastereomer → cis/trans

cis: usually have a dipole moment, often experience steric hindrance = higher energy molecule

30
Q

epimers

A

diastereomer → differentiations only at one chiral center

*** many pairs of carbohydrates are epimers

31
Q

anomers

A

diastereomer → differentiations only in spatial orientation at anomeric carbon of a ring structure

α = OH/OR same side as CH2OH 
β = OH/OR opposite side as CH2OH
32
Q

meso compounds

A

two or more chiral centers that contain a plane of symmetry

33
Q

bases

A

abstract protons

e- dense and have full or partial negative charge

strongest base → forms strongest, most stable bond with hydrogen (acid/base equilibrium prefers the conjugate acid)

34
Q

nucleophiles

A

attack carbons

e- dense and have full or partial negative charge

best nucleophile → reacts the fastest with an available electrophile

35
Q

leaving groups

A

take both e- from the bond with them

best leaving groups → most stable after they leave

36
Q

E1

A

carbocation formed + methyl/hydride shifts

product = planar

favored by → weak bases, 3° C only, polar protic solvents

37
Q

SN1

A

carbocation formed + methyl/hydride shifts

product = racemic mixture

favored by

→

poor nucleophiles,

3° C only, polar protic solvents

38
Q

E2

A

no carbocation + no methyl/hydride shifts

product = planar

favored by → strong and/or bulky bases

39
Q

SN2

A

no carbocation formed + no methyl/hydride shifts

product = inversion of relative configuration

favored by → strong and/or bulky bases, methyl/1°/2° C

40
Q

melting point / boiling point

A

↑ bp + ↑ mp = ↑ chain length/molecular weight
↓ bp = ↑ branching

***straight chain alkanes have highest mp, among branched alkanes → increased branching = ↑ mp

41
Q

alkenes

A

nucleophiles + weakly e- withdrawing

stability: tetrasubstituted > trisubstituted > disubstituted > mono substituted > unsubstituted

42
Q

ethers

A

very non-reactive + weakly polar

most non-polar species are soluble in ethers

low boiling point → no H bonding

***make excellent solvents

43
Q

basicity

A

function of thermodynamics → describes how much the molecule wants to react, not how quickly

44
Q

nucleophilicity

A

function of kinetics → describes how easily/readily a molecule will react, but not how stable the new bond will be

45
Q

basicity vs nucleophilicity

A

steric hindrance → favors basicity

reactivity (low stability) → favors basicity

46
Q

carbocations

A

mechanisms will always proceed through the most stable carbocation (unless peroxide is present)

stability: 3° > 2° > 1°

47
Q

polar protic

A

capable of H bonding
favor SN1
water, methanol, ethanol, ammonia, acetic acid

48
Q

formal charge

A

= (valence e-) - (non-bonding valence e- in lone pairs) - (# of bonds)

49
Q

sp

A

linear

180°

50
Q

alcohols

A

less acidic than water

acidity: 3° > 2° > 1°

51
Q

polar aprotic

A

cannot form H bonds
favor SN2
tetrahydrofuran (THF), acetone, dimethylforamide (DMF), acetonitrile (MeCN), dimethylsulfoxide (DMSO)

52
Q

alcohol oxidation

A

1° alcohol → aldehyde → carboxylic acid
2° alcohol → ketone
3° alcohol → cannot be oxidized further

oxidizing agents: O3, Cr2O7, CrO4, KMnO4, Jones, Collins, PCC, PDC

53
Q

alcohol reduction

A

NaBH4 → can only reduce aldehydes and ketones

LiAlH4 and H2/pressure → can reduce aldehydes, ketones, carboxylic acids, esters

MCAT (15 decks)

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