OCHEM Flashcards by Madeline Wing

attracted to and react with positive atoms

nucleophiles

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C-C=N

imine

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NH2

amine

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C=C-NH

enamine

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NH2-C=O

amide

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cyclic amides

lactams

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cyclic esters

lactones

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produces another ester and alcohol

transesterification

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why amides have a high boiling point:

they can form intermolecular H bonds

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most reactive to nucleophilic substitution:

stable leaving group (large atomic radius)

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reactivity of carboxylic acid derivatives from highest to lowest:

acid halides>anhydrides>esters>amides

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primary alcohols that react with PCC form:

aldehydes

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secondary alcohols that react with PCC form:

ketones

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most acidic hydrogen on a compound

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

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

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

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reaction that deals with a nucleophilic attack and change in stereochemistry

SN2 reactions

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SN2 reaction causes what to happen to a molecules stereochemistry

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

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

nucleophilic attack

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ketone body transported in the bloodstream

acetoacetate

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difference b/t primary and tertiary alcohol

primary can be oxidized

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same formula but atoms are arranged differently on molecule

structural isomers

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more H’s than -OH’s means

more acidic

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primary alcohol oxidized to what

aldehydes

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secondary alcohol oxidized to what

ketones

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weak oxidizing reagent

PCC

most acidic H's

attached to alpha carbon; so alpha H's

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

nucleophiles

example of a strong base or nucleophile

OH-

great electrophile

C=O (carbonyl)

leads to 1 carbonyl and 1 double bond

aldol condensation

without protons

aprotic

Jones reagent

CrO3, H2SO4, acetone

what reagent oxidizes sugar

Tollen's

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

SN2 rxn

what protects aldehydes and ketones

diols

can accept electrons and they are positive

electrophiles

nucleophilic substitution/carbocation; protic solvent

SN1

enol to ketone

keto-enol tautomerization

converting b/t linear and cyclic forms of sugars

mutarotation

strong oxidizing reagents (oxygen rich)

KMnO4, Na2Cr2O7, Jones Reagent, H2CrSO4

weak oxidizing reagent (partial)

PCC

strong reducing agent (H rich)

LiAH4

weak reducing agent

NaBH4

reduces aldehydes/ketones to alcohols

LiAH4 and NaBH4

polar aprotic rxn

SN2

polar protic rxn

SN1

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

nucleophilicity

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

a change in bond dipole moment

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

excitation of bound electrons

this contains either a ketone or aldehyde with a hydroxy group

aldol

reaction that occurs during peptide bond formation; what is byproduct

condensation/dehydration reaction; water is byproduct

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

enantiomers

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

diastereomers

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

aqueous impurities

cannot separate the enantiomers if the molecule is what

not chiral

during recrystallization, what is more soluble than the other

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

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

the trans product b/c less steric hindrance

enone consists of

double bond and a ketone

enal consists of

double bond and an aldehyde

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

aldol addition

what alcohol will most likely undergo substitution by SN1 mechanism?

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

most soluble saturated fatty acid in water

the one with the shortest alkyl chain

carboxylate

carboxylic acid without the H on OH

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

gel electrophoresis

bond that links monosaccharides together in an oligosaccharide

glycoside bond

size exclusion chromatography is also known as what

gel filtration chromatography

most common leaving groups:

weak bases large groups with resonance halogens

racemic mixtures and meso compounds are optically what

inactive

conjugation makes a molecule less or more stable

separates compounds based on polarity and size

chromatography

separates DNA and proteins based on their size

gel electrophoresis