CA and CAD Key
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Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key
1. Name the following compounds.
Cl (a) propanoyl chloride
O
O (b) isopropyl acetate O
N (c) N-ethyl-N-methylacetamide
O
O
(d) C O phenyl benzoate
CH3
(e) H (S)-3-hydroxybutanoic acid CH CO H HO 2 2
O (f) E-2-methyl-2-butenoic acid HO
(g) 2-ethyl-4-methylhexanoic acid
CO2H
O O
(h) acetic butanoic anhydride O Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key
2. Draw structures for the following compounds.
O (a) Octanoyl chloride
Cl
OH O (b) Ethyl 3-hydroxybutanoate
O
(c) N-Cyclohexylpentanamide O
N H
(d) Propanoic anhydride O O
O
(e) Formic propanoic anhydride O O
H O
O (f) 2-Pentynoic acid C C
HO
O (g) 10-Undecenoic acid
HO
CO2H (h) 2-Methylbenzoic acid
CH3 Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key
3. Provide reagents by each arrow below to complete the following reaction scheme.
Br CO2H CH2OH 1. Mg, Et2O 2. CO2 + 1. LAH, 2. H O+ 3. H3O 3
H2CrO4
CO2H CO2CH3 CO2H
+ - + H2O, H or OH CH3OH, H
SOCl2
C(O)Cl CO2H CHO 1. LAH + 2. H3O H2O, pyridine 3. PCC
N2H4, KOH
CH2OH CO2H CH3
+ 1. LAH, 2. H3O KMnO4
PCC
CHO CO2H CO2C(O)CH3
1. SOCl2 H2CrO4 2. CH3CO2Na Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key
4. Each of the following conversions requires more than one step. Show reagents and experimental conditions necessary to bring about each conversion.
O O (a)
H OCH3
O O O H2CrO4 CH3OH
H H2SO4 OH OCH3
CH3 CH2CO2CH2CH3 (b)
CH3 CH2Br CH2MgBr Br2 Mg
h Et2O
1. CO 2+ 2. H3O
CH2CO2CH2CH3 CH2CO2H CH3CH2OH
H+ Dr. Caroline Clower Chemistry 2412 Carboxylic Acids and Derivatives Key
CH3 O (c) C NO2
H2N
Cl
CH3 CH3 CH3
Cl Cl HNO3 2
H2SO4 FeCl3
NO2 NO2
- 1. KMnO4, OH , 2. H+
CO2H C(O)NH2 C(O)Cl
Cl Cl Cl SOCl 2 NH3 2
NO2 NO2 NO2 O
C Dr. Caroline Clower Chemistry 2412 H3C OH Carboxylic Acids and Derivatives Key
5. What is the order of decreasing activity (most reactive = 1, least reactive = 4) towards 1 7 nucleophilic acyl substitution for the following carboxylic acid derivatives? 2 3 4 5 6
O O O O O
H C C O C CH H C C N(CH ) H C C O CH (CH ) CH C O CH O 3 O 3 O 3 3 2 O 3 3 O 3 2 3 8 9 10 C 1 C C 4 C 2 C 3 H3C Cl H3C O CH3 H3C OCH2CH3 H3C NH2
11 12 13 14 15 16 17 18 19 20
6. Draw the major organic products formed from the following reactions or sequences of reactions.
O O OH OH NH2 C H (a) 1. LiAlH4, ether OH + 2. H3O
CH3 C Ph
C Ph CH2OH O O
O O
OH OCH3 HCl (b) + CH3OH H2O
O excess OH MgBr + (c) H3O CH3CH2 C CH2CH2CH3 Cl ether
CH2CH2CH3
H N
+ N SOCl2 LiAlH4 H3O (d) CO2H