11: Carboxylic Acids and Its Derivatives (Part 3)

Question 1

1° and 2° amides contain one or two N – H bonds that are capable of?

Answer 1

intermolecular hydrogen bonding

Question 2

Carboxylic derivatives contain an ____________ bonded to an electronegative atom Z that can serve as a leaving group

Answer 2

acyl group

Question 3

these do not undergo nucleophilic acyl substitution

Answer 3

aldehydes and ketones

Question 4

rank the carboxylic acid derivatives from the most stable to least stable

Answer 4

1. amides
2. esters
3. acid anhydrides
4. acyl chlorides

Question 5

hydrolysis of an ester is called?

Answer 5

saponification

Question 6

these also react with ammonia and 1° and 2° amines to form 1°, 2°, and 3° amides, respectively

Answer 6

acid chlorides

Question 7

Acid chlorides react with oxygen nucleophiles to form?

Answer 7

anhydrides
carboxylic acids
esters

Question 8

Carboxylic acid derivatives having > 5 C’s are ___________ because the nonpolar alkyl portion is too large to dissolve in the polar H2O solvent

Answer 8

H2O insoluble

Question 9

As the basicity of Z increases, the stability of ________ increases because of added resonance stabilization

Answer 9

RCOZ

Question 10

this occurs when the leaving group Z is a weaker base and therefore better leaving group than the attacking nucleophile

Answer 10

nucleophilic substitution

Question 11

Most carboxylic acid derivatives having ___________ are H2O soluble because they can hydrogen bond with H2O

Answer 11

≤ 5 C’s

Question 12

it is the least stable carboxylic acid derivative because Cl– is the weakest base.

Answer 12

acid chloride

Question 13

Most carboxylic acid derivatives having ≤ 5 C’s are _____________ because they can hydrogen bond with H2O

Answer 13

H2O soluble

Question 14

A weak base like ____________ is added to the reaction mixture to remove this strong acid, forming an ammonium salt

Answer 14

pyridine

Question 15

The better the leaving group, the more reactive RCOZ is in?

Answer 15

nucleophilic acyl substitution

Question 16

Acid chlorides also react with ________ and ___________________ to form 1°, 2°, and 3° amides, respectively

Answer 16

ammonia
1° and 2° amines

Question 17

These compounds undergo nucleophilic acyl substitution

Answer 17

carboxylic acid derivatives

Question 18

these are named as alkane derivatives

Answer 18

nitriles

Question 19

Acid chlorides react with ____________________ to form anhydrides, carboxylic acids, and esters

Answer 19

oxygen nucleophiles

Question 20

A weak base like pyridine is added to the reaction mixture to remove this strong acid, forming an?

Answer 20

ammonium salt

Question 21

Any nucleophile that is also a ________________ will react with a carboxylic acid by removing a proton first, before any nucleophilic substitution reaction occurs

Answer 21

strong base

Question 22

these are hydrolyzed in acid or base to form carboxylic acids or carboxylate anions.

Answer 22

amides

Question 23

Any ____________ that is also a strong base will react with a carboxylic acid by removing a proton first, before any nucleophilic substitution reaction occurs

Answer 23

nucleophile

Question 24

Carboxylic derivatives contain an acyl group bonded to an electronegative atom Z that can serve as a _____________.

Answer 24

leaving group

Question 25

Carboxylic acid derivatives having _______ are H2O insoluble because the nonpolar alkyl portion is too large to dissolve in the polar H2O solvent

Answer 25

> 5 C’s

Question 26

soap is prepared by the basic hydrolysis or saponification of a?

Answer 26

triacylglycerol

Question 27

Carboxylic acid derivatives are _________ in organic solvents regardless of size.

Answer 27

soluble

Question 28

carboxylic acid derivatives undergo?

Answer 28

nucleophilic acyl substitution

Question 29

it is the most stable carboxylic acid derivative because –NR’2 is the strongest base

Answer 29

amide

Question 30

these have higher boiling points and melting points than compounds of comparable and molecular weight

Answer 30

amides