Ch.21

Question 1

Name this carboxylic acid derivative:

R - C =– N (triple bond)

Answer 1

nitrile

Question 2

define carboxylic acid derivatives

Answer 2

compounds with functional groups that can be converted to carboxylic acids by a simple acidic or basic hydrolysis

Question 3

______ are carboxylic derivatives in which the hydroxy group (-OH) is replaced by an alkoxy (-OR).

Answer 3

esters

Question 4

what are lactones?

Answer 4

cyclic esters

Question 5

Ammonium salts are converted to _____ at high temperatures.

Answer 5

amides

Question 6

What are lactams?

Answer 6

cyclic amides

Question 7

The atoms at the ends of the triple bonds (RCN) are ____ hybridized.

Answer 7

sp

Question 8

the atoms at the ends of the triple bonds (RCN) have a bond angle of ____

Answer 8

180

Question 9

Acid halides are also called what?

Answer 9

acyl halides

Question 10

acid halides are ____ derivatives used in the synthesis of other acyl compounds such as esters.

Answer 10

activated

Question 11

How are acid halides named?

Answer 11

replacing the -ic acid suffix name with -yl and the halide name

Question 12

What does the word anhydride mean?

Answer 12

without water

Question 13

Acid anhydrides are ___ derivatives of carboxylic acids

Answer 13

activated

Question 14

How are anhydrides named?

Answer 14

replacing the word acid with anhydride

Question 15

What is the nomenclature of multifunctional compounds? (the order of presedence)

Answer 15

acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine > alkene, alkyne

Question 16

The physical properties of acid derivatives largely depends on what?

Answer 16

their polarity and hydrogen bonding properties

Question 17

What is the polarity nature of amides?

Answer 17

strongly polar

Question 18

Are acid derivatives soluble in common organic solvents?

Answer 18

yes

Question 19

Most acid derivatives have C=O stretches between ____ and ____

Answer 19

1700 cm-1 and 1800 cm-1

Question 20

Interconversion of acid derivatives occurs by _____ __________ ________

Answer 20

nucleophilic acyl substitution

Question 21

Nucleophilic acyl substitutions are also called what?

Answer 21

acyl transfer reactions

Question 22

What do nucleophilic acyl substitutions do?

Answer 22

transfer the acyl group to the attacking nucleophile

Question 23

In a SN2 reaction, the bond forming and bond-breaking steps are simultaneous and the reaction is _______

Answer 23

endothermic

Question 24

In the nucleophilic acyl substitution, the elimination of the alkoxide is highly ______.

Answer 24

exothermic

Question 25

What is transesterification?

Answer 25

when one alkoxy group can be replaced by another with acid or base catalyst (large excess of desired alcohol used)

Question 26

What is saponification?

Answer 26

the base-catalyzed hydrolysis of ester

Question 27

How are soaps made?

Answer 27

by heating NaOH with a fat (triester of glycerol) to produce the sodium salt of a fatty acid

Question 28

What can DIBAL ((i-Bu)2AlH) reduce?

Answer 28

esters to aldehydes

Question 29

Grignard and organolithium reagents add twice to acid chlorides and esters to give _____ after protonation.

Answer 29

alcohols

Question 30

What are Gilman reagents?

Answer 30

dialkylcuprates

Question 31

Acid chlorides react once with dialkylcuprates to give _______

Answer 31

ketones

Question 32

A reaction of a nitrile with a grignard or organolithium reagent produces a ______

Answer 32

ketone

Question 33

What is a strong dehydrating agent that can eliminate the elements of water from a primary amide to give a nitrile.

Answer 33

POCl3 or P2O5

Question 34

Five-membered lactams and six-membered lactams often form on _______ or adding a dehydrating agent to the appropriate amino acid.

Answer 34

heating

Question 35

Beta-Lactams are what?

Answer 35

Unusually reactive, four-membered ring amides are capable of acylating a variety of nucleophiles

Question 36

What are beta-lactams found in?

Answer 36

penicillins, cephalosporins, and carbapenems

Question 37

How do beta-lactams work?

Answer 37

by interfering with the synthesis of bacterial cell walls

Question 38

What is a thioester formed from?

Answer 38

a carboxylic acid and a thiol

Question 39

Thioesters are _____ reactive toward nucleophilic acyl substitution than are normal esters.

Answer 39

more

Question 40

How effective is the resonance overlap in a thioester compared to an ester.

Answer 40

The resonance overlap in a thioester is not as effective as that in an ester.

Question 41

What is Coenzyme A (CoA)?

Answer 41

a thiol whose thioesters serve as a biochemical acyl transfer reagent

Question 42

Acetyl CoA transfers an acetyl group to a _______, with coenzyme A serving as the leaving group.

Answer 42

nucleophile

Question 43

What is acetyl choline?

Answer 43

a neurotransmitter, at the skeletal neuromuscular junction and those synapses when acetylcholine receptors are located

Question 44

When acetylcholine esterase (AChE) is inhibited what happens?

Answer 44

excess acetyl choline builds up in the synapse

Question 45

What are polycarbonates?

Answer 45

polymers bonded to the carbonate ester linkage

Question 46

Reaction of toluene diisocyanate with ethylene glycol produces one of the most common forms of ___________.

Answer 46

polyurethanes