Carboxylic Acid Derivatives

Question 1

condensation products of carboxylic acids and ammonia or amines

Answer 1

amides

Question 2

condensation products of carboxylic acids with alcohols (Fischer Esterification)

Answer 2

esters

Question 3

condensation dimers of carboxylic acids

Answer 3

anhydrides

Question 4

order of reactivity of carboxylic acid derivatives in nucleophilic substitution reactions

Answer 4

anhydrides, esters, then amides

Question 5

describes when a reaction cannot proceed (or significantly slows) because of substituents crowding the reactive site

Answer 5

steric hindrance

Question 6

groups, such as acetals, that can be used to increase steric hindrance or otherwise decrease the reactivity of a particular portion of a molecule

Answer 6

protecting groups

Question 7

refers to uneven distribution of charge across a σ bond because of differences in electronegativity; the more electronegative groups in a carbonyl-containing compound, the greater its reactivity

Answer 7

induction

Question 8

refers to the presence of alternating single and multiple bonds, which creates delocalized π electron clouds above and below the plane of the molecule; electrons experience resonance through the unhybridized p-orbitals, increasing stability; conjugated carbonyl containing compounds are more reactive because they can stabilize their transition state

Answer 8

conjugation

Question 9

increased amounts can make a molecule more reactive; β-lactams are prone to hydrolysis because they have significant ring ____

Answer 9

strain

Question 10

is due to torsional strain from eclipsing interactions and angle strain form compressing bond angles below 109.5°

Answer 10

ring strain

Question 11

splits an anhydride in two by the addition of a nucleophile

Answer 11

cleavage reaction

Question 12

cleavage reaction:

nucleophile thats addition results in an amide and a carboxylic acid

Answer 12

addition of ammonia or an amine

Question 13

cleavage reaction:

nucleophile thats addition results in an ester and a carboxylic acid

Answer 13

addition of an alcohol

Question 14

cleavage reaction:

nucleophile thats addition results in two carboxylic acids

Answer 14

addition of water

Question 15

the exchange of one esterifying group for another on an ester; the attacking nucleophile is an alcohol; one ester is simply transformed into another one

Answer 15

transesterification

Question 16

can be hydrolyzed to carboxylic acids under strongly acidic or basic conditions; the attacking nucleophile is water or the hydroxide ion

Answer 16

amides