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7/23/2019 4.5 Answers to Exercises
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13.5 ANSWERS TO EXERCISES
13.5 Exercise 1
1.
a) propanoic acid b) propan-1-ol c) no reaction
C
O
C
H
C
H
H
HOH
H
C C C
H
H
H H
H
HOH
H
d) propan-2-ol e) 2-hydroxymethylpropanenitrile
H C
H
HC
H
C
H
H
H
OH
CH3
OH
C NC
CH3
f) butanoic acid g) methylpropanoic acid h) no reaction
C C C C
H
H
H H
O
OH
H
H H
CC
H
H
H C
H
OH
O
CH
H
H
i) 2-hydroxy,2-methylbutanenitrile
CH3
OH
C NCH2
C
CH3
2. a) CH3CH2COCH3 + 2H! CH3CH2CH"OH)CH3
HO
H
:H-
:
C
O
H
-
+C H
OH
OH-
C
O
δ
+
-
CH3
CH3
CH2
CH3
CH2
CH3
CH3
CH3
CH2
b) CH3CH2COCH3 + HC# CH3CH2CH"CH3)C#
CH3
CH3
CH3
δ
+
δ
H CN
-
δ
δ
+
-
CCH3CH
2
O
:CN-
CH3CH
2C CN
H+
O:CCH
3CH
2 CN
OH
-
3. a) propanal and HC# b) butanone and HC# c) methylpropanal and HC#
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13.5 Exercise 2
1. a) CH3CH2COOH + #aOH CH3CH2COO- #a+ + H2O
b) 2CH3CH2CH2COOH + #a2CO3 2CH3CH2CH2COO- #a+ + CO2 + H2O
c) HCOO-
#a+
+ HCl HCOOH + #aCld) 2CH3COO- #a+ + H2$O% 2CH3COOH + #a2$O%
e) 2CH3CH"CH3)COOH + #a2CO3 2CH3CH"CH3)COO- #a+ + CO2 + H2O
2. a) CH3CH2COOH + CH3OH && CH3CH2COOCH3 + H2O
organic product & methyl propanoate
b) CH3COOH + CH3CH"OH)CH3 && CH3COOCH"CH3)CH3 + H2Oorganic product & methylethyl ethanoate
c) HCOOH + CH3CH2CH2OH && HCOOCH2CH2CH3 + H2O
organic product & propyl methanoated) CH3CH2CH2COOH + CH3CH2CH2CH2OH && CH3CH2CH2COOCH2CH2CH2CH3 + H2O
organic product & butyl butanoate
3. a)
C
O
OH
H CH3
CH2
OH+ H
2O
+C
O
O CH2
CH3
H
b)
O Na- ++ NaOH +
CH3 C
O
O CH3
CH2
C
O
CH3
CH2
CH3
OH
c)
OH+ H
2O
H
CH
CH3
CH3+
CH3
C
O
O CH3
CH3
OH
CC
O
C
H
H
H
d)
CH2CH
2H C
O
CH3
OH+CH
2 CH2
H C
O
O CH3
O Na- +
+ NaOH
%.a)
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C
C
C
H
H
H
H
H
OH
OH
OH
+
C
C
C
H
H
H
H
H
O C
O
O C
O
C15
H31
O C
O
C15
H31
C15
H31
C15
H31
C
O
3+ 3H
2O
OH
b)
+ 3NaOH
C
C
C
H
H
H
H
H
OH
OH
OH
+
C
C
C
H
H
H
H
H
O C
O
O C
O
C15
H31
O C
O
C15
H31
C15
H31
C15
H31
C
O
Na O+ -
3
'eaction "a) ta(e place in the tomach
*he fatty acid are ued in cell membrane*he glycerol i ued a an energy ource
'eaction "b) i carried out indutrially
*he glycerol i ued in pharmaceutical and cometic preparation*he carboxylate alt are ued a oap
13.5 Exercise 3
1. a) CH3CH2COCl + #H3 CH3CH2CO#H2 + HCl
organic product propanamide b) "CH3CH2CH2CO)2O + CH3CH"OH)CH3 CH3CH2CH2COOCH"CH3)CH3 + CH3CH2CH2COOH
organic product methylethyl butanoate and butanoic acidc) HCOCl + CHCH#H HCO#HCHCH + HCl
organic product #-ethyl methanamide
d) "CH3CO)2O + CH3CH"#H2)CH3 CH3CO#HCH"CH3)CH3 + CH3COOH
organic product #-methylethylethanamide and ethanoic acid
e) CH3CH"CH3)COCl + H2O CH3CH"CH)COOH + HClorganic product methylpropanoic acid
2. a)
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C
O
Cl
C
H
H
H
CH3
CH2
OH+
b)
+C
H
H
H
C
H
C
Cl
O
H
CH3
NH2
c)
C
O
Cl
C
H
+ CH3
OH
CH3
CH3
CH2
d)
C
Cl
O
H + CH3 CH
2 NH
2
e)
+C
O
O
C
O
CH3
CH3
C
O OH
O H
3. a)
..
..
δ
H
C
Cl
O
δ
+
-
N
H
C
O
Cl
H
-
+N
H
C
O
H+
Cl-
N
H
C
O
H
+ HCl
N
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
b) nucleophilic addition-elimination
c) acid anhydride i cheaper than acyl chloride
the acid anhydride reaction i le iolent
the acid anhydride reaction doe not produce toxic fume of HCl
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