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chapter 18 > carboxyl derivatives > Flashcards

carboxyl derivatives Flashcards

1
Q

what is an acid chloride

A

an acyl group attached to a halogen

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2
Q

how do you name an acid chloride

A

ic–> yl halide

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3
Q

what does a sulfonyl chloride look like

A

an s double bonded to 2 o’s and replace the oh with a cl

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4
Q

what does a carboxylic anhydride look like

A

2 acyl groups bonded to an O

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5
Q

what are the 2 different types of anhydrides

A

mixed and symmetrical

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6
Q

how do you name an acid anhydride

A

replace the acid with anhydride

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7
Q

what does a cyclic anhydride look like

A

it is a cyclic version of an anhydride ( to acyl groups bonded to an o

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8
Q

what does a phosphoric ester look like

A

it has 2 phosphoral groups bonded to an o atom

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9
Q

what is a carboxylic ester

A

an acyl group bonded to an or or oar

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10
Q

how do you name a carboxylic ester?

A

ic–> -ate

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11
Q

what is a lactone

A

a cyclic ester

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12
Q

how do you name a lactone

A

ic acid–> olactone

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13
Q

when naming a lactone which is number one

A

the carbonyl oxygen is number 1

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14
Q

what does an amide look like

A

it is an acyl group bonded to an nitrogen atom

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15
Q

how do you name an amide

A

drop the oic acid and add amid

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16
Q

what is a lactam

A

a cyclic amide

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17
Q

what is an imide

A

2 acyl groups bonded to an oxygen

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18
Q

what is the functional group of a nitrile

A

it is a cyano

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19
Q

how do you name a nitrile group

A

drom the oic acid and add onitrile

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20
Q

amides have the same acidity as what

A

alcochols

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21
Q

what 2 things are more acidic than amides

A

sulfonamides and imides

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22
Q

do amides dissolve in naoh

A

no

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23
Q

doe sulfanomides dissolve in naoh

A

yes

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24
Q

do imides dissolve in naoh

A

yes

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25
Q

out of amide , ester , acid halide and acid anhydride determine the order of reactivity from most to least

A

acid halide , acid anhydriide , ester, amide

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26
Q

what explains the reactivity trend

A

leaving group ability

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27
Q

fischer esterification occurs by what what kind of mechansim

A

nucleophil acyl substitution

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28
Q

describe what happens in fisher esterification

A

carboxylic acid + alcohol = ester

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29
Q

what is the reagent for fisher esterification

A

h2so4

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30
Q

is the fisher reaction reversible

A

yes

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31
Q

is we have an ester and we do a fisher esterification what do we get

A

an alcohol and an carboxylic acid

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32
Q

if something is stable what does it say about the leaving group

A

it has a good leaving group

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33
Q

do high or low molecular weight ions react rapidly with water to form carboxylic ions

A

low

34
Q

if you add an acid chloride + water =

A

carboxylic acid and hcl

35
Q

are acid chlorides reactive

A

yes! they are so reactive that they do not require an acid or a base

36
Q

do low or high molecular weight anhydrides react readly with water to give 2 molecules of carboxylic acid

A

low

37
Q

acid anhydride + water =

A

2 mols of carbooxylic acid

38
Q

if you want to hydrolize an ester what do you need

A

an ester or a base

39
Q

what is the opposite of a fisher esterification called

A

hydrolysis of an ester in acid

40
Q

when hydrolyzing an ester what is the role os the acid catalyst

A

it is to protenate the carbonyl oxygen and increase electrophillic character

41
Q

can you hydrolize an ester in neutral ph

A

no

42
Q

what is the principal of microscopic reversibility

A

a principal that states for any reversible reaction the sequence of intermediates and transition states must be the same but in reverse

43
Q

what is the reverse of adding a proton

A

taking a proton away

44
Q

what is the reverse of nucleophillic attack

A

leaving group departure

45
Q

what 2 reactions follow the principal of microscopic reversibility

A

fisher esterification and hydrolysis of an ester under acidic conditions

46
Q

what is another name for hydrolysis of an ester under basic conditions

A

saponificaton

47
Q

ester hydrolysis in a base is acid or base promoted

A

base

48
Q

if you hydrolized an ester in acid what is the product

A

a carboxylic acid

49
Q

if you hydrolize an ester under basic conditions what do you get

A

sodium acetate

50
Q

if you want to hydrolyze an ester what do you do

A

add 2 h20 and h2so4

51
Q

if you hydrolyze a nitrile what do you get

A

a carboxylic acid

52
Q

what do you get when an acid chloride reacts with alcohol

A

carboxylic acid and ester

53
Q

if you have a cyclic anhydride and react it with alcohol what do you get

A

one ester group and one carboxyl group

54
Q

when you react an ester with an alcohol what do you get

A

the 2 things come together

55
Q

how do you prepare a sulfonic ester

A

it is the reaction of an alkane or tscl with alcohol or phenol

56
Q

when you react an acid anhydride with water what do you get

A

one mole of ester and one mole of carboxylic acid

57
Q

what happens when you react an acid halide with ammonia

A

you get an amide , the nh2 replaces the halide

58
Q

if you react an acid anhydride with ammonia what do you get

A

you get to amides, one gets an nh2 and the other gets an nh4

59
Q

what happens if you react an ester with ammonia

A

the r group breaks off and the nh2 replaces it

60
Q

are esters more or less reactive than acid halides

A

then are less

61
Q

when you react an acid chloride with a salt of carboxylic acid what do you get

A

the 2 come together but nacl comes out

62
Q

if you treat formic ester with with 2 moles of grignard what do you get

A

a 2 alcohol

63
Q

what does formic ester look like

A

H co double bond , och3

64
Q

when you react an ester with 2 moles of gringard what do you get

A

a 3 alcohol

65
Q

grignard reagent is similar to which other reagent

A

RLi

66
Q

what is the difference between grignard and rLi

A

RLi is more powerful

67
Q

if you react an ester with RLi what do you get

A

a tertiary alcohol

68
Q

what is the gilman reagent

A

(Ch3)2CuLi

69
Q

gilman reagent must be at what temp

A

-78

70
Q

if you use gilaman on an acid chloride what do you get

A

a ketone , the halide will fall off and a ch3 will form

71
Q

what do gilman reagents only react with

A

acid cholorides

72
Q

if you reduce an ester with LiAlH4 what do you get

A

2 alcohols

73
Q

if there are any double bonds on an ester and you use LiAlH4 will anything happen

A

yes , they will come off

74
Q

if you want to reduce an ester to an aldehyde what can you use

A

dibalh

75
Q

ester + dibalh =

A

aldehyde

76
Q

does NabH4 reduce esters

A

no

77
Q

does nabh4 reduce ketones

A

yes

78
Q

does nabh4 reduce aldehydes

A

yes

79
Q

can nabh4 reduce amides

A

yes

80
Q

amide + nabh4

A

amine ( the c=0 goes away)

81
Q

what can you use to reduce a nitrile to a amine

A

LiAlH4

chapter 18 (3 decks)

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