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GAMSAT Chemistry organic reaction pathways > 8. Carboxylic Acids & Derivatives > Flashcards

8. Carboxylic Acids & Derivatives Flashcards

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1
Q

what has the greatest and least acidity of the following

phenol, alcohols, COOH

A

COOH > phenols > alchols

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2
Q

what does e- donating substituents do to the acidity or acid strength and pka

A

decrease acid strength

increase pka

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3
Q

what does e- accepting substituents do to the acidity or acid strength and pka

A

increase acid strength

decrease pka

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4
Q

what are the 3 ways COOH is prepared

A

oxidation of alcohol

Grignard addition to CO2

nucleophilic substitution of alkyl halide

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5
Q

what reagents or reactants are needed to prepare COOH from alcohol oxidation

A

primary alcohol

H2CrO4

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6
Q

what reagents or reactants are needed to prepare COOH from Grignard addition to CO2

A
  1. RMgX + CO2
  2. H3O+
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7
Q

what reagents or reactants are needed to prepare COOH from nucleophilic substitution of alkyl halide

A
  1. CN-
  2. H3O+

add CN- to halide RX and then react with acid to get COOH

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8
Q

what does COOH react with metals to produce

A

salt and H2 gas

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9
Q

what does COOH react with metal carbonates to produce

A

salt, water and CO2

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10
Q

what are the 3 types of acid derivatives

A

acyl chlorides and anhydrides

esters

amides

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11
Q

how are acyl chlorides prepared, what reagents and reactants are required

A

COOH + SOCl2

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12
Q

how are symmetrical anhydrides prepared, what reagents and reactants are required

A

RCOOH + P2O5

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13
Q

what is produced when COOH + P2O5

A

symmetrical anhydrides

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14
Q

how are unsymmetrical anhydrides prepared, what reagents and reactants are required

A

RCOOH + RClC=O = both symmetrical and unsymmetrical anhydrides

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15
Q

what is produced when RCOOH + RClC=O

A

both symmetrical and unsymmetrical anhydrides

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16
Q

to produce an amide from an acyl chloride what reactants and reagents are required

A

+H2NR

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17
Q

to produce an COOH from an acyl chloride what reactants and reagents are required

A

+H2O

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18
Q

to produce an ester from an acyl chloride what reactants and reagents are required

A

+ROH

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19
Q

to produce an anhydride from an acyl chloride what reactants and reagents are required

A

+RCO2H

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20
Q

to produce an tertiary alcohol from an acyl chloride what reactants and reagents are required

A

1.RMgX
2. H3O+

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21
Q

what is produced when acyl chlorides react with +HN-R

A

amide

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22
Q

what is produced when acyl chlorides react with +H2O

A

COOH

23
Q

what is produced when acyl chlorides react with +ROH

A

ester

24
Q

what is produced when acyl chlorides react with RCO2H

A

anhydride

25
Q

what is produced when acyl chlorides react with 1. RMgX and 2. H3O+

A

tertiary alcohol

26
Q

to produce a amide from an acid anhydrideswhat reactants and reagents are required

A

+R-NH2

27
Q

to produce a COOH from an acid anhydrideswhat reactants and reagents are required

A

+H2O

28
Q

to produce a ester from an anhydride what reactants and reagents are required

A

+ROH

29
Q

what is produced when acid anhydrides react with +R-NH2

A

amide

30
Q

what is produced when acid anhydrides react with +H2O

A

COOH

31
Q

what is produced when acid anhydrides react with +ROH

A

ester

32
Q

can acid anhydrides form acyl chlorides why

A

no cant convert directly to acyl chloride as its less reactive than acyl chlorides

33
Q

how do you prepare esters - 2 ways

A

acid anhydrides/halides + alcohol

or

COOH + alcohol via H+

34
Q

what are the 2 reactions esters undergo

A

nucleophillic acyl substitution

hydrolysis

35
Q

to produce an amide from an ester what reactants and reagents are required

A

+RNH2

36
Q

to produce an primary alcohol from an ester what reactants and reagents are required

A
  1. LiAlH4
  2. H3O+
37
Q

to produce an tertiary alcohol from an ester what reactants and reagents are required

A
  1. 2RMgX
  2. H3O+
38
Q

what is produced when esters react with +RNH2

A

amides

39
Q

what is produced when esters react with

  1. LiAlH4
  2. H3O+
A

primary alcohol

40
Q

what is produced when esters react with

  1. 2RMgX
  2. H3O+
A

tertiary alcohol

41
Q

to produce an COOH and R-OR group from an ester what reactants and reagents are required

A

H2O/H3O+

or

H2O/OH-
(base will cause carboxylate ion or COO-)

42
Q

how are amides prepared

A

acid halide/anhydride + amine

43
Q

how are primary amides produced, what reagents and reactants are needed

A

+NH3

ammonia

44
Q

how are secondary amides produced, what reagents and reactants are needed

A

+ R-NH2

primary amine

45
Q

how are tertiary amides produced, what reagents and reactants are needed

A

+ R2-NH

secondary amine

46
Q

what are amides

A

RCO-NR2

47
Q

what are the 3 reactions amides can undergo

A

hydrolysis

nucleophillic acyl substitution

polyamide formation

48
Q

for an amide to undergo hydrolysis what reactants or reagents are required

A

70% aq H2SO4/heat

49
Q

for an amide to undergo nucleophillic acyl substitution to form amines and water what reactants or reagents are required

A

+OH-

50
Q

for an amide to undergo polyamide formation what reactants or reagents are required

A

diacid chloride + diamine

via HCl

51
Q

what is produced when amides undergo hydrolysis via 70% H2SO4 aqueous/heat

A

R-NH3+ + RCOO-

52
Q

what is produced when amides undergo nucleophillic acyl substitution with OH-

A

RNH2 + H2O

53
Q

what is produced when amides undergo polyamide formation via HCl

A

forms amide bond

(-CO-NH-)

GAMSAT Chemistry organic reaction pathways (12 decks)

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