Carboxylic Acids and Their Derivatives: Nucleophilic Addition-Elimination at the Acyl Carbon

P1: PCX/SRB JWCL338-17
P2: xxx JWCL338-Solomons-v1
Printer: Bind Rite May 5, 2010 14:17
17
CARBOXYLIC ACIDS AND THEIR DERIVATIVES: NUCLEOPHILIC ADDITIONELIMINATION AT THE ACYL CARBON
SOLUTIONS TO PROBLEMS
17.1 (a) 2-Methylbutanoic acid (b) (Z )-3-Pentenoic acid or (Z )-pent-3-enoic acid (c) Sodium 4-bromobutanoate (d) 5-Phenylpentanoic acid (e) (E)-3-Ethyl-3-pentenoic acid or (E)-3-Ethylpent-3-enoic acid 17.2 Acetic acid, in the absence of solvating molecules, exists as a dimer owing to the formation of two intermolecular hydrogen bonds:
O O
H H
O O
At temperatures much above the boiling point, the dimer dissociates into the individual molecules.
O
17.3 (a) F (F is more electronegative than H)
OH O
(F is more electronegative than Cl)
(b) F
OH O
(Cl is more electronegative than Br)
(c) Cl
OH F O
(F is closer to CO2 H)
(d)
OH O
(e)
OH (F F
is closer to
CO2 H)
402
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CARBOXYLIC ACIDS AND THEIR DERIVATIVES
403
(f) Me3N
O OH
[Me3 N
is more electronegative than H ]
O
(g) CF3 (CF3 is more electronegative than CH3 )
OH O
17.4 (a)
O OCH3 O O OCH3
(b) O2N O (d) N CH3 O
(c)
CH3O
CH3
(e)
CN
(f ) O
OCH3 OCH3
O (g) O O (i) Br Br ( j) O O (h) H
O CH3 N CH3 O O O O O
17.5 (a)
(1) KMnO4, OH , heat (2) H3O+
OH
+ CO2
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404
O Br (b)
Mg Et2O
MgBr
CO2
OMgBr H3O+ O OH
O (c)
(1) Cl2/NaOH (2) H3O+
O OH + CHCl3
O (d)
OH
O (e) OH
OH
O (f ) H
(1) KMnO4, OH (2) H3O+
O OH
17.6 These syntheses are easy to see if we work backward using a retrosynthetic analysis before writing the synthesis.
(a) Retrosynthetic analysis OH O O Synthesis Br

Mg Et2O
MgBr + C
Br
O OH O
MgBr
(1) CO2 (2) H3O+
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405
(b) Retrosynthetic analysis O MgBr OH + O Synthesis Br Mg

Et2O
Br
C MgBr
O O
(1) CO2 (2) H3O+
OH
+ O (c) Retrosynthetic analysis O MgBr OH O Synthesis Br + C O O

Mg Et2O
Br
MgBr + O C O
(1) CO2 (2) H3O+
OH
(d) Retrosynthetic analysis O OH + O Synthesis Br

Mg Et2O
MgBr
Br
O O
(1) CO2 (2) H3O+
MgBr + O C O
OH
(e) Retrosynthetic analysis O OH
MgBr O Synthesis Br Mg
Et2O
Br
+ C
O O
MgBr (1) CO2

(2) H3O+
OH
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406
17.7 (a)
OH O
Retrosynthetic analysis
OH O
Synthesis
Br
Br O OH
CN
H3O+ heat
OH O
O OH
Synthesis
Br
Br
(1) CN (2) H3O+,
O OH
O OH
O OH
Synthesis
Br O OH Br
would
Br
(1) CN (2) H3O+, heat
(b) A nitrile synthesis. Preparation of a Grignard reagent from HO not be possible because of the presence of the acidic hydroxyl group. 17.8 Since maleic acid is a cis dicarboxylic acid, dehydration occurs readily: O O
OH OH O Maleic acid
200 C
O + H2O O Maleic anhydride
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407
Being a trans dicarboxylic acid, fumaric acid must undergo isomerization to maleic acid rst. This isomerization requires a higher temperature.
O HO OH O Fumaric acid
17.9
heat
O OH OH O
H2O
O O O
The labeled oxygen atom should appear in the carboxyl group of the acid. (Follow the reverse steps of the mechanism in Section 17.7A of the text using H2 18 O.)
+
H
HO
H O OCH3 O H
+
17.10
O OCH3
H A
O OCH3
Intermolecular proton transfer
O O
A
O O + HOCH3
H O O
H O H
+
CH3
17.11 (a) (1)
+ C6H5SO2Cl OH A
OH , heat (inversion)
OSO2C6H5 OH + C6H5SO3
B O (2) + OH C O
OH , heat (retention)
C6H5
Cl O C6H5 O O
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+ C6H5 D OH
408
H (3) ( )
4
O Br + O Na+
(inversion)
O O E
H ( )
4
+ NaBr
OH , heat (retention)
H HO F ( )
4
O + O Na+
H (4) ( ) Br
4
OH , heat (inversion)
H HO F ( )
4
Br
(b) Method (3) should give a higher yield of F than method (4). Since the hydroxide ion is a strong base and since the alkyl halide is secondary, method (4) is likely to be accompanied by considerable elimination. Method (3), on the other hand, employs a weaker base, acetate ion, in the SN 2 step and is less likely to be complicated by elimination. Hydrolysis of the ester E that results should also proceed in high yield. 17.12 (a) Steric hindrance presented by the di-ortho methyl groups of methyl mesitoate prevents formation of the tetrahedral intermediate that must accompany attack at the acyl carbon. (b) Carry out hydrolysis with labeled 18 OH in labeled H2 18 O. The label should appear in the methanol.
O O
17.13 (a) C6H5
OH H2O
O +
+
C6H5 O C6H5 O
H3O+ H2O
OH +
O (b) N H
OH H2O
NH2 O
H3O+ H2O
HO
NH3
+
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409
O O HO
(c)
OH H2O
O NH2 +
O
NH2 C6H5
N O H
NH2 C6H5
H3O+ H2O
O HO
NH3
O + HO
NH3 C6H5
17.14 (a)
OH O
P4O10 heat
SOCl2
Cl O
NH3
NH2 O
CN
(b) An elimination reaction would take place because CN is a strong base, and the substrate is a 3 alkyl halide.
NC
Br
HCN
Br
O CH2OH
17.15 (a)
O +
CH2 O
C N H
O (b) Cl C Cl + 4 CH3NH2
O C
CH3N
H O
NCH3 + 2 CH3NH3 + 2 Cl
H
CH2 (c) O
C Cl +
H3NCH2CO2 CH2 O
OH
O C N H CH2CO2 + Cl
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410
O CH2 (d) O C N H CO2 O CH2 (e) C O N H CH2CO2

HBr CH3CO2H
CH2CO2
H2 Pd
H3NCH2CO2
+ CH3
H3NCH2CO2H + CH2Br CO2 +
O (f ) H2N C
OH , H2O
NH2
heat
2 NH3
CO32
17.16 (a) By decarboxylation of a -keto acid:
O OH
100150 C
O + CO2
(b) By decarboxylation of a substituted malonic acid:
O HO
O OH
100150 C
O OH + CO2
(c) By decarboxylation of a -keto acid:
O OH
100150 C
O + CO2
(d) By decarboxylation of a substituted malonic acid:
O HO
O OH
100150 C
O OH + CO2
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17.17 (a) The oxygen-oxygen bond of the diacyl peroxide has a low homolytic bond dissociation energy (DH 139 KJ mol1 ). This allows the following reaction to occur at a moderate temperature.
O R O O
O R 2 R
O O H 139 kJ mol1
(b) By decarboxylation of the carboxyl radical produced in part (a).
O R O R + CO2
(c) Chain Initiation
O Step 1 R O Step 2 R O O O
O
heat
O R 2 R O
+ CO2
Chain Propagation Step 3 Step 4 R R + + R R
Steps 3, 4, 3, 4, and so on.
Problems
Structure and Nomenclature
O OH O
17.18 (a)
(b)
H OH
(c)
HO NO2
(d)
Cl
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412

O OCH3 NH2 O O OH F
(e)
(f) HO
O
OH
(g) HO
(h) H
N CH3
CH3
O O O O CH3 O
(i)
(j)
(k) CH3CN
(l)
OH O OH O
(m)
(n) HO
O
OH
17.19 (a) 2-phenyl ethanamide (b) trans-2-butendioic acid (c) benzene 1,2-dicarboxylic acid (d) 3-phenyl propanoyl chloride (e) benzonitrile (f) tert-butyl propanoate (g) phenyl acetic anhydride (h) formamide
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O OH O OH O OH
413
17.20
<
<
<
F F F
OH
17.21 (a) The conjugate base of an amide is stabilized by resonance.
O R NH2 + B R
O NH + BH
O R
NH
This structure is especially stable because the negative charge is on oxygen.

There is no resonance stabilization for the conjugate base of an amine, RNH . (b) The conjugate base of an imide is stabilized by additional resonance structures,
O R
O + OH R
O N
O R + H2O
NH R An imide
O R N
O R
O R
Functional Group Transformations
O
17.22 (a)
OH OH + HCl (b)
O (c) O (d)
O NH2
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414
O (e) CH3 + H3C
O O (f ) H
O (g) ONa (h)
O N H CH3 + CH3 N+ H H H Cl
O ( i) N CH3 O (k) O
17.23 (a) CH3 CONH2 + CH3 CO2 NH4 + (b) 2 CH3 CO2 H (c) CH3 CO2 CH2 CH2 CH3 + CH3 CO2 H (d) C6 H5 COCH3 + CH3 CO2 H (e) CH3 CONHCH2 CH3 + CH3 CO2 CH3 CH2 NH3 + (f ) CH3 CON(CH2 CH3 )2 + CH3 CO2 (CH3 CH2 )2 NH2 +
CH3
CH3 N+ CH3
H H
O Cl ( j) O
O (l)
O O
O
17.24 (a)
O NH4 O O
O (b) OH HO O O
H2N
(c)
OH O O O
+
(d) O O (f) N O
OH
O H3N O
O H2N
(e)
N H
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O
18 18
415
17.25 (a)
O
OH + OH HO
(b)
O HO
(c) No Reaction
(d)
OH O
(e)
(f)
O-Na+ + OH
17.26 In ethyl amine, the lone pair of electrons on nitrogen is readily available to accept a proton from hydrochloric acid and form the salt. In the case of the amide the lone pair of electrons on the nitrogen is not as able to accept a proton from hydrochloric acid and form the salt. The reason for this lack of salt formation is the presence of the adjacent carbonyl group in the amide. With the carbonyl group adjacent to the nitrogen atom, the lone pair of electrons on the nitrogen is delocalized into the carbonyl group. This delocalization makes the electrons less available to serve as a proton acceptor, hence the lack of any appreciable salt formation upon treatment of the amide with HCl.
O
17.27 (a)
O O O O
(b)
OH [(Z) + (E)] O
(c) O O O (e) NH
(d)
O O O
(f)
NH
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416
General Problems
O
17.28 (a)
O O
(b)
NH2 O OH
(c)
(d)
OH
(e)
OH O
(f)
(g)
OH O
HO
(h)
FIRST PAGES
417
O
17.29 (a)
OH
(1) H2CrO4 (2) CH3OH (excess), H2SO4 (cat.)
OCH3
O
(b)
O O
(1) NaOH, H2O (2) H3O+
OH OH
(c)
(1) H2O, H2SO4 (cat.) (2) SOCl2
O Cl
N O
(d)
LiAlH
( (
O
O H O
Cl O
(e)
OCH3 O NH
LiAlH
O
HCl, H2O
OH
(f)
NH3 Cl
+
O
17.30 (a)
O Cl
SH
O
(b)
NH2
O HN
Cl
N
O
(c)
OH
O HO
O O
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418
O O
(d)
H2SO4 (cat.)
HO
OH O +
O OH
(e)
O AlCl3
HO
CH3 CH3
17.31 (a) H3C

CH3
(b)
OTs
CN O OH
(c)
OH
(d) CH3(CH2)7CH=CH(CH2)7CH2OH
O O Na
(e)
FIRST PAGES
419
Mechanisms 17.32 (a) Acid-Catalyzed Hydrolysis

O H NH2 H OH2 - H2O
OH NH2
OH NH2
NH2
OH OH2 NH2 H
HO
OH2 NH2 -H +H+

+
HO
OH NH3
O - NH3
O H2O -H OH + NH4
OH
OH2
(b) Base-Catalyzed Hydrolysis

O Na NH2 OH H2O O OH NH2 + NH3 + O OH OH
O O Na
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420
17.33 (a)
O OH H OH2 - H2O
OH OH
OH O H
OH
H OH OH HO HO O OH -H+ +H+
HO
O OH2 - H2O
O -H
H2O OH2
O O
O Na OH H2O NH2
OH NH2
O OH
(b)
+ NH3 +
OH
O O Na
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421
(c)
C
OH2 - H2O
H C
H OH2 C H -H H H H2O - H2O H
N O
OH2 H2O H
C H
N O
C H
N O
H H2O NH2 -H OH2
O NH2
17.34 Performing iodolactonization reactions under slightly basic conditions generates the carboxylate anion. This carboxylate anion serves as the nucleophile in the attack on the cyclic iodonium ion intermediate, to yield the lactone product. Having the carboxylate anion present when the cyclic iodonium ion is formed helps facilitate the reaction.
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422
Synthesis
O CH3
17.35 (a)
OH Cl O
Cl O (b) Cl [from (a)] OH CN Cl CH3 (c) Cl CN OH
(1) SOCl2 (2) LiAlH
HCN
Et2O, 78 C
Cl
OH
H3O+, H2O heat
OH Cl O Br Cl O OH
NaCN
NBS hv or ROOR CCl4
H3O+, H2O heat
Cl O OH
(1) SOCl2
Cl O H HO CN
(d) Cl [from (c)]
HCN
(2) LiAlH O
( (
HO
Et2O, 78 C
Cl
Cl
O OH Cl Cl [(E) + (Z)]
O OH
H3O+, H2O heat
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423
17.36 (a) HO
OH
O HO O O OH
OH (b)
HO O
OH
17.37 (a)
OH
O OH O
(b)
Br
(1) Mg, Et2O (2) CO2
H3O+
OMgBr O OH
Br
CN
CN
H3O+, H2O heat
O OH
(1) KMnO4, OH , heat
O 2 OH
(c) [(E) or (Z)] O (d) H
(2) H3O+
(1) Ag(NH3)2+OH (2) H3O+
O OH
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CH3 CH3 HNO3 H2SO4 NO2 remove any ortho-isomer O CH3 KMnO4 heat O2N O2N O OH H2N OH + O2N CH3
17.38
Sno HCl
17.39
SOCl2
AlCl3
O OH See text, p. 691

(1) C6H5MgBr (2) NH4Cl/H2O HA heat
O Cl O Br
NBS hv or ROOR
C6H5
OH
C6H5
C6H5
ONa
C6H5
FIRST PAGES
425
H
17.40 (a)
CO2H C C
CO2H CO2H
+ H H
CO2H CO2H C C H H CO2H C C H CO2H
H H
CO2H CO2H
(b)
+ HO2C
(c)
CO2H CO2H
17.41 (a)
TsCl, pyridine
OH (R)-()-2-butanol
H2SO4, H2O (retention)
(retention)
OTs
CN (inversion)
CN
(1) LiAlH4
CO2H (+) C
(2) H2O (retention)
() D
OH
(b) OH
PBr3 pyridine (inversion)
Br E
CN (inversion)
CN F
(R)-()-2-butanol
H2SO4, H2O (retention)
(1) LiAlH4
CO2H () C
(2) H2O (retention)
OH (+) D
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426
(c) OTs A
O (inversion)
O G O
OH (retention)
O + OH (+) H (S)-(+)-2-butanol O
(d) OH () D
PBr3 (retention)
Mg
Br J
(1) CO2
diethyl ether (retention)
MgBr K O (e) HO H
(2) H3O+ (retention)
CO2H L OH OH + HO OH CN HO HO M O OH N O OH
[O] HNO3
HCN
HO OH
CN
CN
OH (R)-(+)-Glyceraldehyde
CN HO HO O OH OH
(f ) M
H2SO4, H2O heat
HO HO P O OH
HO
HO OH meso-Tartaric acid O O OH
(g) N
H2SO4, H2O heat
HO HO Q OH
OH
[O] HNO3
HO
HO OH ()-Tartaric acid
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427
O
17.42
H OH
Br2, H2O [O]
O H
OH OH OH
PBr3
O H
OH Br OH
OH
(R)-(+)Glyceraldehyde
(R)-()Glyceric acid
(S )-()-3-Bromo2-hydroxypropanoic acid
H3O+ heat
O H
OH O
O H
OH
NaCN
CN OH (R)-(C4H5NO3)
OH OH (R)-(+)-Malic acid
H
17.43 (a)
HO
OH H O
HCN
H HO HO M
OH
H H
CN + HO H N
OH
CN
[cf. Problem 17.41(e)]
OH
(R)-(+)Glyceraldehyde N
H2SO4 H2O
H HO H
OH
O OH
[O] HNO3
HO
H O H
OH
O OH
OH
OH
()-Tartaric acid [cf. Problem 17.41(g)] O HO O H OH OH

Zn H3O+
HO
Br O H
O OH OH
PBr3
(S)-()-Malic acid
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428
(b) Replacement of either alcoholic produces the same stereoisomer.
OH by a reaction that proceeds with inversion
H HO
2
OH O
1
PBr3
Br HO O H
H O OH OH HO
H O Br
OH O OH H
OH (inversion OH
at C2)
O H
PBr3 (inversion at C1)
H HO
2
OH O
1
OH OH
O H
(c) Two. The stereoisomer given in (b) and the one given next, below.
H HO
2
OH
1
PBr3
H HO O H
Br O OH OH HO
H O H
OH
O OH Br
OH (retention OH
at C2)
O H
PBr3 (retention at C1)
H HO
2
OH O
1
OH OH
O H
(d) It would have made no difference because treating either isomer (or both together) with zinc and acid produces ( ) malic acid.
HO
Br O H
O OH
Zn
O HO O H OH OH ()-Malic acid
OH H3O+
H Zn + HO H3O O H
Br
O OH OH
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17.44 (a) CH3O2C
CO2CH3 . This is a Diels-Alder reaction.
(b) H2 , Pd. The disubstituted double bond is less hindered than the tetrasubstituted double bond and hence is more reactive. (c) CH2 (d) LiAlH4
CH O
CH
CH2 . Another Diels-Alder reaction.
(e) CH3
S O
Cl and pyridine
(f) CH3 CH2 S (g) OsO4 , then NaHSO3 (h) Raney Ni (i) Base. This is an aldol condensation. (j) C6 H5 Li (or C6 H5 MgBr) followed by H3 O+ (k) H3 O+ . This is an acid-catalyzed rearrangement of an allylic alcohol.
O
(l) CH3CCl, pyridine , (m) O3 , followed by oxidation (n) Heat Spectroscopy
O
17.45
O Phenacetin
N H
OH, H2O reflux
O O Phenetidine NH2 + O
An interpretation of the 1 H NMR spectral data for phenacetin is as follows: O (c)
(a)
O (d)
N H (e)
(b)
(a) triplet 1.4 (b) singlet 2.1 (c) quartet 3.95 (d ) doublet 6.8; doublet, 7.4 (e) broad singlet 9.0
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17.46 (a)
(c) (a) O
O (b)
(b) O
O (c)
(a)
Interpretation: (a) Triplet 1.2 (6H) (b) Singlet 2.5 (4H) (c) Quartet 4.1 (4H)
O , 1740 cm1 (ester) O
O
(b)
(c) O H (b)
(a)
(d )
Interpretation:
(a) O , 1720 cm1 (ester) O
(a) Doublet 1.0 (6H) (b) Multiplet 2.1 (1H) (c) Doublet 4.1 (2H) (d ) Multiplet 7.8 (5H)
(b)
(c)
O O (c)
(a)
(d )
Interpretation: (a) Triplet 1.2 (3H) (b) Singlet 3.5 (2H) (c) Quartet 4.1 (2H) (d ) Multiplet 7.3 (5H)
(b) H
(d)
O OH (a)
OH, 25002700 cm1 O , 1705 cm1 (acid) OH
Cl Cl
Interpretation: (a) Singlet 6.0 (b) Singlet 11.70
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Cl
(e) (b) H H (b)
O O
(c) (a)
Interpretation: (a) Triplet 1.3 (b) Singlet 4.0 (c) Quartet 4.2
17.47 That compound X does not dissolve in aqueous sodium bicarbonate indicates that X is not a carboxylic acid. That X has an IR absorption peak at 1740 cm1 indicates the presence of a carbonyl group, probably that of an ester (Figure 17.2). That the molecular formula of X (C7 H12 O4 ) contains four oxygen atoms suggests that X is a diester. The 13 C spectrum shows only four signals indicating a high degree of symmetry for X. The single signal at 166.7 is that of an ester carbonyl carbon, indicating that both ester groups of X are equivalent. Putting these observations together with the information gathered from DEPT 13 C spectra and the molecular formula leads us to the conclusion that X is diethyl malonate. The assignments are
(c) (a)
O O (d) (b)
O (d) O
(a) 14.2
(c) (a)
(b) 41.6 (c) 61.3 (d) 166.7
17.48 The very low hydrogen content of the molecular formula of Y (C8 H4 O3 ) indicates that Y is highly unsaturated. That Y dissolves slowly in warm aqueous NaHCO3 suggests that Y is a carboxylic acid anhydride that hydrolyzes and dissolves because it forms a carboxylate salt:
O R R O O (insoluble)
NaHCO3 H2O, heat
O R + O O Na+
R O Na+ (soluble)
The infrared absorption peaks at 1779 and 1854 cm1 are consistent with those of an aromatic carboxylic anhydride (Figure 17.2). That only four signals appear in the 13 C spectrum of Y indicates a high degree of symmetry for Y. Three of the signals occur in the aromatic region ( 120 - 140) and one signal is downeld ( 162)
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These signals and the information from the DEPT 13 C NMR spectra lead us to conclude that Y is phthalic anhydride. The assignments are O (a) O O (b) (d) (c) (a) 125 O O OH (b) 130 OH OH (c) 136 O O O (d) 162 Y Z AA Z is phthalic acid and AA is ethyl hydrogen phthalate. Challenge Problems 17.49 (a) Ethyl acetate (b) Acetic anhydride (c) N-Ethylacetamide.
17.50 In the rst instance, nucleophilic attack by the amine occurs preferentially at the less hindered carbon of the formyl group. (Recall that aldehydes are more reactive than ketones toward O nucleophiles for the same reason.) In the second case, F is a better leaving group O O F F than H since the former is the conjugate base of the stronger acid. O H H O O CH3 OH O Cl O N H 17.51
COCl2 CH3NH2
O
17.52 C6H6
O Cl
AlCl3 Clemmensen reduction
O H H HCl, ZnCl2
Cl
KCN
CN
CN
NaNH2 CH3I H3O+ heat
OH
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O
17.53 A =
O C =
B = D = (racemic)
In the last step, HI/red P accomplishes both the reduction of of the nitrile function. OH to H and the hydrolysis
CN
17.54 (a) The signal at 193.8 is consistent with the carbonyl carbon of an aldehyde and shows that the PCC reaction produced cinnamaldehyde. (b) The signal at 164.5 is consistent with the carbonyl carbon of a carboxylic acid, and suggests that the oxidation with K2 Cr2 O7 in sulfuric acid produced cinnamic acid.
QUIZ
17.1 Which of the following would be the strongest acid? (a) Benzoic acid (b) 4-Nitrobenzoic acid (d) 4-Methoxybenzoic acid (e) 4-Ethylbenzoic acid 17.2 Which of the following would yield (S )-2-butanol? (c) 4-Methylbenzoic acid
O
(a) (R)-2-Bromobutane (b) (R)-2-Bromobutane (c) (S)-2-Butyl acetate (d) All of the above (e) None of the above 17.3 Which reagent would serve as the basis for a simple chemical test to distinguish between hexanoic acid and hexanamide? (a) Cold dilute NaOH (c) Cold concd H2 SO4 (e) None of these (b) Cold dilute NaHCO3 (d) More than one of these
O Na+
product
OH , H2O heat
OH , H2O heat OH , H2O heat
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17.4 Give an acceptable name for:
O Cl O OH A B
OCH3
NHCH3
NO2
17.5 Complete the following synthesis.
A O (a) CH3 OH C O Cl D
(CH3)2NH
(CH3)2NH2+ Cl
E O O O 2 F
NH2 OH
+ C6H5 OH
H + C6H5NH+ C6H5 H A
O O
O (b) Cl B + + CH3
18
OH
+ HCl
C
NaOH, H2O heat
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O (c) Cl
NH3(xs)
A + NH4+ Cl
P4O10, heat
(1) DIBAL-H hexane, 78 C (2) H2O
17.6 Which of these acids would undergo decarboxylation most readily?
O
(a)
O OH
(b)
O OH
O
(c)
O OH
(d)
OH O
O
(e)
OH
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Carboxylic Acids and Their Derivatives: Nucleophilic Addition-Elimination at the Acyl Carbon

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P1: PCX/SRB JWCL338-17

P2: xxx JWCL338-Solomons-v1

Printer: Bind Rite May 5, 2010 14:17

P1: PCX/SRB JWCL338-17

P2: xxx JWCL338-Solomons-v1

Printer: Bind Rite May 5, 2010 14:17