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Kaplan Organic Chemistry > Ch. 9: Carboxylic Acid Derivatives > Flashcards

Ch. 9: Carboxylic Acid Derivatives Flashcards

1
Q

how are amides, esters, and anhydrides all formed

A

condensation reactions with carboxylic acids

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2
Q

what are amides

A

carbonyl with alpha nitrogen

RCONR2

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3
Q

what kind of amines will form amides with a carboxylic acid

A

primary and secondary only, amine must lose a hydrogen

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4
Q

what are cyclic amides called

A

lactams

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5
Q

what are esters

A

carbonyl with alpha ether

RCOOR

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6
Q

what occurs during a fischer esterification

A

acidic conditions: carboxylic acids + alcohols –> esters

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7
Q

what are cyclic esters called

A

lactones

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8
Q

carboxylic acid vs ester boiling point

A

carboxylic acid > esters

esters cannot hydrogen bond

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9
Q

carboxylic acid vs amides boiling point

A

???

hydrogen boding depends on number of alkyl groups present

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10
Q

what functional group links carboxylic acids and glycerol

A

esters

triacylglycerols are formed by esters of long chain carboxylic acids (fatty acids) and glycerols

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11
Q

what occurs during saponification

A

fats are hydrolyzed to produce soaps

[rCOO- + Na]

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12
Q

how are anhydrides formed

A

carboxylic acid condensation

RCO + RCO

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13
Q

carboxylic acid vs anhydride

A

carboxylic acid < anhydride

anhydrides must have a much greater weight than their carboxylic acid derivatives

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14
Q

what are cyclic anhydrides called

A

phthalic or succinic anhydrides

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15
Q

ordered reactivity of amides, anhydrides, carboxylic acids, and esters to nucleophilic substitution

A

anhydrides > carboxylic acids = esters > amides

most electrophilic least electrophilic

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16
Q

what does induction refer to

A

distribution of charge across sigma bonds

electronegative atoms create partial positive charges on their adjacent atoms

17
Q

what does conjugation refer to

A

alternating single and multiple bonds, delocalizing electrons throughout the entire pi system

18
Q

what are enones

A

alpha, beta - unsaturated carbonyl system

conjugated carbonyl structure

19
Q

what occurs during a cleavage reaction

A

molecule splits in two

20
Q

what occurs during a nucleophilic acyl substitution of an anhydride

A

nucleophile (ammonia, alcohol) attacks one carbonyl (that acts as an electrophile) and the other carbonyl becomes the leaving group

21
Q

what will revert an anhydride back to carboxylic acids

A

water

22
Q

what occurs during transesterification

A

alcohol acts as an nucleophile that attacks an ester (acting as an electrophile) and one ester is transformed to another as the original -OR group leaves and is replaced with that of the nucleophile

23
Q

what will revert an amide back to a carboxylic acid

A

acid to protonate (or base to attack) + water

Kaplan Organic Chemistry (8 decks)

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