Ch. 9: Carboxylic Acid Derivatives

Question 1

how are amides, esters, and anhydrides all formed

Answer 1

condensation reactions with carboxylic acids

Question 2

what are amides

Answer 2

carbonyl with alpha nitrogen

RCONR2

Question 3

what kind of amines will form amides with a carboxylic acid

Answer 3

primary and secondary only, amine must lose a hydrogen

Question 4

what are cyclic amides called

Answer 4

lactams

Question 5

what are esters

Answer 5

carbonyl with alpha ether

RCOOR

Question 6

what occurs during a fischer esterification

Answer 6

acidic conditions: carboxylic acids + alcohols –> esters

Question 7

what are cyclic esters called

Answer 7

lactones

Question 8

carboxylic acid vs ester boiling point

Answer 8

carboxylic acid > esters

esters cannot hydrogen bond

Question 9

carboxylic acid vs amides boiling point

Answer 9

???

hydrogen boding depends on number of alkyl groups present

Question 10

what functional group links carboxylic acids and glycerol

Answer 10

esters

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

Question 11

what occurs during saponification

Answer 11

fats are hydrolyzed to produce soaps

[rCOO- + Na]

Question 12

how are anhydrides formed

Answer 12

carboxylic acid condensation

RCO + RCO

Question 13

carboxylic acid vs anhydride

Answer 13

carboxylic acid < anhydride

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

Question 14

what are cyclic anhydrides called

Answer 14

phthalic or succinic anhydrides

Question 15

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

Answer 15

anhydrides > carboxylic acids = esters > amides

most electrophilic least electrophilic

Question 16

what does induction refer to

Answer 16

distribution of charge across sigma bonds

electronegative atoms create partial positive charges on their adjacent atoms

Question 17

what does conjugation refer to

Answer 17

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

Question 18

what are enones

Answer 18

alpha, beta - unsaturated carbonyl system

conjugated carbonyl structure

Question 19

what occurs during a cleavage reaction

Answer 19

molecule splits in two

Question 20

what occurs during a nucleophilic acyl substitution of an anhydride

Answer 20

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

Question 21

what will revert an anhydride back to carboxylic acids

Answer 21

water

Question 22

what occurs during transesterification

Answer 22

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

Question 23

what will revert an amide back to a carboxylic acid

Answer 23

acid to protonate (or base to attack) + water