Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 14.2, Problem 14.1P
Calculate the nominal mass of each ion. Unless otherwise indicated, use the mass of the most abundant isotope of each element.
(a) 
(b) 
(c) 
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36) Complete the following multi-step reactions showing applications of enolate ions arising from ketones,
esters, malonic ester, and keto ester, etc.
(30 pts)
(1)
A
NaOH, H₂O+
heat
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NaOEt
EtO
OEt
(11)
EOH, H+
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B
LDA, H₂O+
-78°C
B
(i) NaOMe, Et-Br
(ii) H₂O+, heat
EtOOC
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COOEt
B
A
(i) NaOEt
LiAlH
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H₂O+
(ii) H3O+, heat
Write the mechanism for Aldol Condensation (I A or B), and Claisen Condensation (II A).
31) Complete two sets of reactions involving (R)-4-methyl-pent-2-ol producing racemic mixture of tertiary
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(25 pts)
O
OH
0
K2Cr2O7
Ph-CH2-Br, Mg,
H2SO4
THF, H3O*
(A)
(D)
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TsCl, Py
(B)
KCN, DMSO
Ph-CH2-Br, Mg,
THF, H3O+
(C)
Mechanism for reactions B and C:
Manoharan Mariappan, Ph.D., Dept. of Natur. Sci., NFC, Tallahassee, FL
33) Synthesize the aromatic compound containing para-substituted carbonyl compound starting from
benzene. Illustrate the mechanism for reaction A.
1)
NU
(25 pts)
A
FeCl
B
(i) HNO3, H2SO4
(II) Sn, HCl(aq)
NH₂
NO₂-D NH₂
(i) MeCO2Me, heat
C
(ii) K2Cr2O7/H2SO4
D
(ii) SOCl2
(iii) 2 Et-NH2
Mechanism for reaction for the nitration of alkyl benzene (B-i):
Characterize the product compound arising from the reaction D by IR and IH NMR spectral data:
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Chapter 14 Solutions
Organic Chemistry
Ch. 14.2 - Calculate the nominal mass of each ion. Unless...Ch. 14.3 - Propose a structural formula for the cation at m/z...Ch. 14.3 - The low-resolution mass spectrum of 2-pentanol...Ch. 14 - Draw acceptable Lewis structures for the molecular...Ch. 14 - The molecular ion for compounds containing only C,...Ch. 14 - For which compounds containing a heteroatom (an...Ch. 14 - The so-called nitrogen rule states that if a...Ch. 14 - Prob. 14.8PCh. 14 - Prob. 14.9PCh. 14 - Prob. 14.10P
Ch. 14 - Determine the probability of the following in a...Ch. 14 - The molecular ions of both C5H10S and C6H14O...Ch. 14 - Prob. 14.13PCh. 14 - Carboxylic acids often give a strong fragment ion...Ch. 14 - For primary amines with no branching on the carbon...Ch. 14 - Prob. 14.16PCh. 14 - A characteristic peak in the mass spectrum of most...Ch. 14 - Predict the relative intensities of the M and M +...Ch. 14 - The mass spectrum of compound A shows the...Ch. 14 - The mass spectrum of compound B, a colorless...Ch. 14 - Write molecular formulas for the five possible...Ch. 14 - Write molecular formulas for the five possible...Ch. 14 - The molecular ion in the mass spectrum of...Ch. 14 - Prob. 14.24PCh. 14 - Following is the mass spectrum of 1-bromobutane....Ch. 14 - Following is the mass spectrum of...Ch. 14 - Following is the mass spectrum of an unknown...Ch. 14 - Following is the mass spectrum of...Ch. 14 - Prob. 14.29PCh. 14 - Following are mass spectra for the constitutional...Ch. 14 - 2-Methylpentanal and 4-methyl-2-pentanone are...Ch. 14 - Prob. 14.32PCh. 14 - Account for the presence of the following peaks in...Ch. 14 - All methyl esters of long-chain aliphatic acids...Ch. 14 - Propylbenzene, C6H5CH2CH2CH3, and isopropyl...Ch. 14 - Account for the formation of the base peaks in...Ch. 14 - Prob. 14.37PCh. 14 - Prob. 14.38P
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