carboxylic acids and their derivatives (pp. 1025-1028
TRANSCRIPT
Espacio deFormaciónMultimodal
Klein, D. (2012). Carboxylic Acids and Their Derivatives. En Organic Chemistry (pp. 1025-1028). USA: Wiley.
Carboxylic Acids and Their Derivatives
Practice Problems 1025
21.43 H O2
21.44 H
21.45
21.46
21.47 parameta
21.48
2 2
2O 2
H2
H5 2
2
2O
21.49
2
2O [H
21.50
OH
O1) xs LAH2) H2O ?(a)
OH
O1) SOCl22) (CH3)2NH, pyridine
?(b)
NH2
OSOCl2 ?(c)
OMe
O1) H3O±
2) CH3COCl, pyridine ?(d)
OMe
O
DIBAH ?(e)
OHO
O O
?(f)
N
H
Cl
O
pyridine ?(g)
O
O
1) xs LAH2) H2O ?
(h)
N
OH3O±
Heat ?(i)
O
OH3O± ?(j)
21.51
O
O
(a) O
O
(b)
2 2
21.52 A F
OH
AD
E
F B
C
2) H2O1) LiAl(OR)3H
[H±]EtOH
Na2Cr2O7H2SO4, H2O
SOCl2
xsNH3
klein_c21_970-1029hr.indd 1025 11/22/10 12:58 PM
1026 CHAPTER 21 Carboxylic Acids and Their Derivatives
21.53
21.54
OH
(a)
N
O
(b)
OH
O(c)
N
O
H
(d)
21.55
BrO
O
(a)
OOH
(b)
BrN
O
(c)
Br
O
(d)
21.56 para
para
21.57
OH
O
Cl
O
O
O O
OR
O
NH2
O
O
H
21.58 meta
N
O
N,N-Diethyl-m-toluamide(DEET)
Br
m-Bromotoluene
?
21.59
O O
O1) Excess MeMgBr2) H3O+ ?
21.60
OH
O
OH
O
OH
O[H±]H2O ±
21.61
Cl Cl
O
Phosgene
klein_c21_970-1029hr.indd 1026 11/22/10 12:58 PM
Practice Problems 1025
21.43 H O2
21.44 H
21.45
21.46
21.47 parameta
21.48
2 2
2O 2
H2
H5 2
2
2O
21.49
2
2O [H
21.50
OH
O1) xs LAH2) H2O ?(a)
OH
O1) SOCl22) (CH3)2NH, pyridine
?(b)
NH2
OSOCl2 ?(c)
OMe
O1) H3O±
2) CH3COCl, pyridine ?(d)
OMe
O
DIBAH ?(e)
OHO
O O
?(f)
N
H
Cl
O
pyridine ?(g)
O
O
1) xs LAH2) H2O ?
(h)
N
OH3O±
Heat ?(i)
O
OH3O± ?(j)
21.51
O
O
(a) O
O
(b)
2 2
21.52 A F
OH
AD
E
F B
C
2) H2O1) LiAl(OR)3H
[H±]EtOH
Na2Cr2O7H2SO4, H2O
SOCl2
xsNH3
klein_c21_970-1029hr.indd 1025 11/22/10 12:58 PM
1026 CHAPTER 21 Carboxylic Acids and Their Derivatives
21.53
21.54
OH
(a)
N
O
(b)
OH
O(c)
N
O
H
(d)
21.55
BrO
O
(a)
OOH
(b)
BrN
O
(c)
Br
O
(d)
21.56 para
para
21.57
OH
O
Cl
O
O
O O
OR
O
NH2
O
O
H
21.58 meta
N
O
N,N-Diethyl-m-toluamide(DEET)
Br
m-Bromotoluene
?
21.59
O O
O1) Excess MeMgBr2) H3O+ ?
21.60
OH
O
OH
O
OH
O[H±]H2O ±
21.61
Cl Cl
O
Phosgene
klein_c21_970-1029hr.indd 1026 11/22/10 12:58 PM
Practice Problems 1027
2
2 2
H O
21.62
S
N
N
N
O
OCF3
Fluphenazine decanoate
21.63
Benzyl acetate
O
O
21.64
Aspartame
N
O OO
NH2
OH
OH
21.65
Cl
O
O
O
Pyridine
OH
(a)
O
O
HO
O
OH1) NaOH2) H3O±(b)
OO
OH
OH
O(c)
1) NaOH2) H3O±
Cl
O
Cl
O
N
O
N
O
H
H
(d)
H2N NH2
Excess pyridine
O
OOH
OH
1) Excess EtMgBr2) H2O(e)
21.66
21.67
O
OO
H3O±
Heat ?21.68
Pivampicillin
NO
SN
O
HNH2
O O O
O
klein_c21_970-1029hr.indd 1027 11/22/10 12:58 PM
1026 CHAPTER 21 Carboxylic Acids and Their Derivatives
21.53
21.54
OH
(a)
N
O
(b)
OH
O(c)
N
O
H
(d)
21.55
BrO
O
(a)
OOH
(b)
BrN
O
(c)
Br
O
(d)
21.56 para
para
21.57
OH
O
Cl
O
O
O O
OR
O
NH2
O
O
H
21.58 meta
N
O
N,N-Diethyl-m-toluamide(DEET)
Br
m-Bromotoluene
?
21.59
O O
O1) Excess MeMgBr2) H3O+ ?
21.60
OH
O
OH
O
OH
O[H±]H2O ±
21.61
Cl Cl
O
Phosgene
klein_c21_970-1029hr.indd 1026 11/22/10 12:58 PM
Practice Problems 1027
2
2 2
H O
21.62
S
N
N
N
O
OCF3
Fluphenazine decanoate
21.63
Benzyl acetate
O
O
21.64
Aspartame
N
O OO
NH2
OH
OH
21.65
Cl
O
O
O
Pyridine
OH
(a)
O
O
HO
O
OH1) NaOH2) H3O±(b)
OO
OH
OH
O(c)
1) NaOH2) H3O±
Cl
O
Cl
O
N
O
N
O
H
H
(d)
H2N NH2
Excess pyridine
O
OOH
OH
1) Excess EtMgBr2) H2O(e)
21.66
21.67
O
OO
H3O±
Heat ?21.68
Pivampicillin
NO
SN
O
HNH2
O O O
O
klein_c21_970-1029hr.indd 1027 11/22/10 12:58 PM
1028 CHAPTER 21 Carboxylic Acids and Their Derivatives
21.69
DexonTM
O
O
O
O
O
O
O
O
21.70
ClCl
OO
HOOH
21.71
N
O
N
H H
O OO
N
H
N
H
21.72 meta
21.73
OH
OOO
(a)
NH2
O
N
(b)
O
N
O
(c)
OMe
O
H
SS
(d)
COOHO
O
(e)
OH
OOH(f)
OO
O
O
(g)
21.74
Acetaminophen(TylenolTM)
N
HOO
H
21.75
OH
OOO
O
O
HO
H3O±
21.76 5H O2A
AA
21.77 H O
21.78
21.79 para
INTEGRATED PROBLEMS
klein_c21_970-1029hr.indd 1028 11/22/10 12:58 PM
Practice Problems 1027
2
2 2
H O
21.62
S
N
N
N
O
OCF3
Fluphenazine decanoate
21.63
Benzyl acetate
O
O
21.64
Aspartame
N
O OO
NH2
OH
OH
21.65
Cl
O
O
O
Pyridine
OH
(a)
O
O
HO
O
OH1) NaOH2) H3O±(b)
OO
OH
OH
O(c)
1) NaOH2) H3O±
Cl
O
Cl
O
N
O
N
O
H
H
(d)
H2N NH2
Excess pyridine
O
OOH
OH
1) Excess EtMgBr2) H2O(e)
21.66
21.67
O
OO
H3O±
Heat ?21.68
Pivampicillin
NO
SN
O
HNH2
O O O
O
klein_c21_970-1029hr.indd 1027 11/22/10 12:58 PM
1028 CHAPTER 21 Carboxylic Acids and Their Derivatives
21.69
DexonTM
O
O
O
O
O
O
O
O
21.70
ClCl
OO
HOOH
21.71
N
O
N
H H
O OO
N
H
N
H
21.72 meta
21.73
OH
OOO
(a)
NH2
O
N
(b)
O
N
O
(c)
OMe
O
H
SS
(d)
COOHO
O
(e)
OH
OOH(f)
OO
O
O
(g)
21.74
Acetaminophen(TylenolTM)
N
HOO
H
21.75
OH
OOO
O
O
HO
H3O±
21.76 5H O2A
AA
21.77 H O
21.78
21.79 para
INTEGRATED PROBLEMS
klein_c21_970-1029hr.indd 1028 11/22/10 12:58 PM