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MCAT > OCHEM > Flashcards

OCHEM Flashcards

1
Q

attracted to and react with positive atoms

A

nucleophiles

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2
Q

C-C=N

A

imine

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3
Q

NH2

A

amine

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4
Q

C=C-NH

A

enamine

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5
Q

NH2-C=O

A

amide

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6
Q

cyclic amides

A

lactams

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7
Q

cyclic esters

A

lactones

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8
Q

produces another ester and alcohol

A

transesterification

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9
Q

why amides have a high boiling point:

A

they can form intermolecular H bonds

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10
Q

most reactive to nucleophilic substitution:

A

stable leaving group (large atomic radius)

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11
Q

reactivity of carboxylic acid derivatives from highest to lowest:

A

acid halides>anhydrides>esters>amides

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12
Q

primary alcohols that react with PCC form:

A

aldehydes

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13
Q

secondary alcohols that react with PCC form:

A

ketones

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14
Q

most acidic hydrogen on a compound

A

alpha H (on alpha carbon-C next to carbonyl carbon)

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15
Q

Why is an aldehyde with a smaller R group more susceptible to nucleophilic attack:

A

b/c less steric hindrance than a ketone or aldehyde with a larger R group

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16
Q

reaction that deals with a nucleophilic attack and change in stereochemistry

A

SN2 reactions

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17
Q

SN2 reaction causes what to happen to a molecules stereochemistry

A

it inverts it (from S to R or vice versa)

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18
Q

increasing amount of electron-withdrawing groups around carbonyl carbon makes it more susceptible to what

A

nucleophilic attack

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19
Q

ketone body transported in the bloodstream

A

acetoacetate

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20
Q

difference b/t primary and tertiary alcohol

A

primary can be oxidized

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21
Q

same formula but atoms are arranged differently on molecule

A

structural isomers

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22
Q

more H’s than -OH’s means

A

more acidic

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23
Q

primary alcohol oxidized to what

A

aldehydes

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24
Q

secondary alcohol oxidized to what

A

ketones

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25
Q

weak oxidizing reagent

A

PCC

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26
Q

most acidic H’s

A

attached to alpha carbon; so alpha H’s

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27
Q

react with positive charges (halogens, alcohols, double bonds); nitrogen in them

A

nucleophiles

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28
Q

example of a strong base or nucleophile

A

OH-

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29
Q

great electrophile

A

C=O (carbonyl)

30
Q

leads to 1 carbonyl and 1 double bond

A

aldol condensation

31
Q

without protons

A

aprotic

32
Q

Jones reagent

A

CrO3, H2SO4, acetone

33
Q

what reagent oxidizes sugar

A

Tollen’s

34
Q

this type of reaction prefers methyl reactants and leads to inversion of relative configuration (S to R; R to S); also deals with aprotic solvent

A

SN2 rxn

35
Q

what protects aldehydes and ketones

A

diols

36
Q

can accept electrons and they are positive

A

electrophiles

37
Q

nucleophilic substitution/carbocation; protic solvent

A

SN1

38
Q

enol to ketone

A

keto-enol tautomerization

39
Q

converting b/t linear and cyclic forms of sugars

A

mutarotation

40
Q

strong oxidizing reagents (oxygen rich)

A

KMnO4, Na2Cr2O7, Jones Reagent, H2CrSO4

41
Q

weak oxidizing reagent (partial)

A

PCC

42
Q

strong reducing agent (H rich)

A

LiAH4

43
Q

weak reducing agent

A

NaBH4

44
Q

reduces aldehydes/ketones to alcohols

A

LiAH4 and NaBH4

45
Q

polar aprotic rxn

A

SN2

46
Q

polar protic rxn

A

SN1

47
Q

increases down periodic table for polar protic solvents; and decreases down table for polar aprotic solvents

A

nucleophilicity

48
Q

what has to happen for an absorption to be noted on IR spectrum

A

a change in bond dipole moment

49
Q

absorption of UV light by organic molecules always results in what process

A

excitation of bound electrons

50
Q

this contains either a ketone or aldehyde with a hydroxy group

A

aldol

51
Q

reaction that occurs during peptide bond formation; what is byproduct

A

condensation/dehydration reaction; water is byproduct

52
Q

if there is only 1 chiral center, what will the stereoisomers be

A

enantiomers

53
Q

there has to be atleast 2 chiral centers for the stereoisomers to be what

A

diastereomers

54
Q

if in organic layer, a water wash would remove what impurities

A

aqueous impurities

55
Q

cannot separate the enantiomers if the molecule is what

A

not chiral

56
Q

during recrystallization, what is more soluble than the other

A

waste product is more soluble; the product being recrystallized is relatively insoluble

57
Q

which product of aldol condensation is more stable: cis or trans

A

the trans product b/c less steric hindrance

58
Q

enone consists of

A

double bond and a ketone

59
Q

enal consists of

A

double bond and an aldehyde

60
Q

aldol addition or condensation when NO dehydration occurs (OH) stays and doesn’t turn into (O))

A

aldol addition

61
Q

what alcohol will most likely undergo substitution by SN1 mechanism?

A

tertiary alcohol since it will produce the most stable carbocation; (SN1 deals with carbocations)

62
Q

most soluble saturated fatty acid in water

A

the one with the shortest alkyl chain

63
Q

carboxylate

A

carboxylic acid without the H on OH

64
Q

separates DNA, RNA, or proteins according to size/ and or charge

A

gel electrophoresis

65
Q

bond that links monosaccharides together in an oligosaccharide

A

glycoside bond

66
Q

size exclusion chromatography is also known as what

A

gel filtration chromatography

67
Q

most common leaving groups:

A

weak bases
large groups with resonance
halogens

68
Q

racemic mixtures and meso compounds are optically what

A

inactive

69
Q

conjugation makes a molecule less or more stable

A

more

70
Q

separates compounds based on polarity and size

A

chromatography

71
Q

separates DNA and proteins based on their size

A

gel electrophoresis

MCAT (6 decks)

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