8. Carboxylic Acids & Derivatives Flashcards

(53 cards)

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

23
Q

what is produced when acyl chlorides react with +ROH

24
Q

what is produced when acyl chlorides react with RCO2H

25
what is produced when acyl chlorides react with 1. RMgX and 2. H3O+
tertiary alcohol
26
to produce a amide from an acid anhydrideswhat reactants and reagents are required
+R-NH2
27
to produce a COOH from an acid anhydrideswhat reactants and reagents are required
+H2O
28
to produce a ester from an anhydride what reactants and reagents are required
+ROH
29
what is produced when acid anhydrides react with +R-NH2
amide
30
what is produced when acid anhydrides react with +H2O
COOH
31
what is produced when acid anhydrides react with +ROH
ester
32
can acid anhydrides form acyl chlorides why
no cant convert directly to acyl chloride as its less reactive than acyl chlorides
33
how do you prepare esters - 2 ways
acid anhydrides/halides + alcohol or COOH + alcohol via H+
34
what are the 2 reactions esters undergo
nucleophillic acyl substitution hydrolysis
35
to produce an amide from an ester what reactants and reagents are required
+RNH2
36
to produce an primary alcohol from an ester what reactants and reagents are required
1. LiAlH4 2. H3O+
37
to produce an tertiary alcohol from an ester what reactants and reagents are required
1. 2RMgX 2. H3O+
38
what is produced when esters react with +RNH2
amides
39
what is produced when esters react with 1. LiAlH4 2. H3O+
primary alcohol
40
what is produced when esters react with 1. 2RMgX 2. H3O+
tertiary alcohol
41
to produce an COOH and R-OR group from an ester what reactants and reagents are required
H2O/H3O+ or H2O/OH- (base will cause carboxylate ion or COO-)
42
how are amides prepared
acid halide/anhydride + amine
43
how are primary amides produced, what reagents and reactants are needed
+NH3 ammonia
44
how are secondary amides produced, what reagents and reactants are needed
+ R-NH2 primary amine
45
how are tertiary amides produced, what reagents and reactants are needed
+ R2-NH secondary amine
46
what are amides
RCO-NR2
47
what are the 3 reactions amides can undergo
hydrolysis nucleophillic acyl substitution polyamide formation
48
for an amide to undergo hydrolysis what reactants or reagents are required
70% aq H2SO4/heat
49
for an amide to undergo nucleophillic acyl substitution to form amines and water what reactants or reagents are required
+OH-
50
for an amide to undergo polyamide formation what reactants or reagents are required
diacid chloride + diamine via HCl
51
what is produced when amides undergo hydrolysis via 70% H2SO4 aqueous/heat
R-NH3+ + RCOO-
52
what is produced when amides undergo nucleophillic acyl substitution with OH-
RNH2 + H2O
53
what is produced when amides undergo polyamide formation via HCl
forms amide bond (-CO-NH-)