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Organic Chemistry II > Ch.21 > Flashcards

Ch.21 Flashcards

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1
Q

Name this carboxylic acid derivative:

R - C =– N (triple bond)

A

nitrile

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2
Q

define carboxylic acid derivatives

A

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

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3
Q

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

A

esters

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4
Q

what are lactones?

A

cyclic esters

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5
Q

Ammonium salts are converted to _____ at high temperatures.

A

amides

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6
Q

What are lactams?

A

cyclic amides

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7
Q

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

A

sp

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8
Q

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

A

180

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9
Q

Acid halides are also called what?

A

acyl halides

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10
Q

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

A

activated

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11
Q

How are acid halides named?

A

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

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12
Q

What does the word anhydride mean?

A

without water

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13
Q

Acid anhydrides are ___ derivatives of carboxylic acids

A

activated

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14
Q

How are anhydrides named?

A

replacing the word acid with anhydride

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15
Q

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

A

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

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16
Q

The physical properties of acid derivatives largely depends on what?

A

their polarity and hydrogen bonding properties

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17
Q

What is the polarity nature of amides?

A

strongly polar

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18
Q

Are acid derivatives soluble in common organic solvents?

A

yes

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19
Q

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

A

1700 cm-1 and 1800 cm-1

20
Q

Interconversion of acid derivatives occurs by _____ __________ ________

A

nucleophilic acyl substitution

21
Q

Nucleophilic acyl substitutions are also called what?

A

acyl transfer reactions

22
Q

What do nucleophilic acyl substitutions do?

A

transfer the acyl group to the attacking nucleophile

23
Q

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

A

endothermic

24
Q

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

A

exothermic

25
Q

What is transesterification?

A

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

26
Q

What is saponification?

A

the base-catalyzed hydrolysis of ester

27
Q

How are soaps made?

A

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

28
Q

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

A

esters to aldehydes

29
Q

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

A

alcohols

30
Q

What are Gilman reagents?

A

dialkylcuprates

31
Q

Acid chlorides react once with dialkylcuprates to give _______

A

ketones

32
Q

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

A

ketone

33
Q

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

A

POCl3 or P2O5

34
Q

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

A

heating

35
Q

Beta-Lactams are what?

A

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

36
Q

What are beta-lactams found in?

A

penicillins, cephalosporins, and carbapenems

37
Q

How do beta-lactams work?

A

by interfering with the synthesis of bacterial cell walls

38
Q

What is a thioester formed from?

A

a carboxylic acid and a thiol

39
Q

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

A

more

40
Q

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

A

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

41
Q

What is Coenzyme A (CoA)?

A

a thiol whose thioesters serve as a biochemical acyl transfer reagent

42
Q

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

A

nucleophile

43
Q

What is acetyl choline?

A

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

44
Q

When acetylcholine esterase (AChE) is inhibited what happens?

A

excess acetyl choline builds up in the synapse

45
Q

What are polycarbonates?

A

polymers bonded to the carbonate ester linkage

46
Q

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

A

polyurethanes

Organic Chemistry II (8 decks)

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