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Question 1

under what mechanism do ketones and aldehydes react

Answer 1

nucleophilic addition

Question 2

under what mechanism do carboxylic acids and derivatives react through

Answer 2

nucleophilic acyl substitution

Question 3

why do carboxylic acids undergo nucleophilic substituion

Answer 3

they have a substituent that act as a good leaving group

Question 4

what is the order of reactivity of carboxylic acid derivatives from greatest to least

Answer 4

acid halides> anhyride> thioyl ester> ester> amide

Question 5

whats the least reactive carboxylic acid derivative

Answer 5

amide

Question 6

whats the most reactive carboxylic acid derivative? why?

Answer 6

acid halides, halogens are good leaving groups

Question 7

for the hierarchy of reactivity, can we react both down and up?

Answer 7

no, we can only react downhill with decreasing reactivity

Question 8

why are acid chlorides useful

Answer 8

they can react downhill and form all other derivatives

Question 9

what are the three ways to make a acid chloride with a carboxylic acid

Answer 9

1.) thionyl chloride SOCl2

2.) oxalyl chloride (COCl)2

3.) PCl5

Question 10

what is the nucleophile in the hydrolysis of acid chlorides

Answer 10

water under basic conditions

Question 11

what is the product of hydrolysis of acid chlorides

Answer 11

carboxylic acids

Question 12

why do we need basic conditions for hydrolysis of acid chlorides

Answer 12

to deprotonate the carbonyl at the end of the reaction

Question 13

when reacting an acid chloride with an alcohol, what is the product

Answer 13

an ester

Question 14

when reacting an acid chloride with an amine NH3 what is the product

Answer 14

amide

Question 15

when reacting an acid chloride with a carboxylate salt, what is the product

Answer 15

an acid anhydride

Question 16

what are two methods of synthesizing acid anhydrides

Answer 16

1.) using carboxylic acid + acid chloride and a base like pyrimidine

2.) by reacting an acid chloride with a carboxylate salt

Question 17

what does hydrolysis under acidic conditions do to a acetic anhydride

Answer 17

it forms 2 carboxylic acids

Question 18

what are the reagents and products of a acid catalyzed fischer esterification

Answer 18

a carboxylic acid is reacted with an alcohol under acidic conditions to form an ester

Question 19

what is the major organic product and byproducts of fischer esterification

Answer 19

the organic product is an ester, the byproducts are water and H+

Question 20

whats the first step in the mechanism of fishcer esterification

Answer 20

activate the carbonyl

Question 21

why do we use a proton transfer in fischer esterification

Answer 21

it forms a good leaving group and forms water as a byproduct

Question 22

is equillibrium favored in fischer esterification?

Answer 22

no it is unfavorable

Question 23

how can we make the fischer esterification reaction favorable

Answer 23

1.) use an alcohol solvent to provide excess reactants

2.) remove water using drying agents like CaCl2, NaSO4, MgSO4

Question 24

what does a base promoted ester hydrolysis do? (sophonification)

Answer 24

cleaves the ether to form a carboxylate salt

Question 25

what is a lactone

Answer 25

a cyclic ester