Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter F, Problem 2PP
Interpretation Introduction
Interpretation:
The products of the given reactions are to be given.
Concept introduction:
Thiols and disulphides undergo
This can be depicted as:
Sulphur ylide acts as a nucleophile and attacks the carbonyl carbon of
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Problem 3.3 Draw mechanisms for each of the following substitution reactions.
Remember that in each case, loss of the leaving group is preceded by coordination
of the leaving group to a Lewis acid such as H+.
(a)
(b)
CH3
CH3
HCl
H3C-
OH
H3C-
Cl
CH3
CH3
OH
ZnCl2
Ar
Ar
Ar
Ar
HO
Problem Three
a) Identify the following as nucleophile or electrophile:
iii) C,H,CHO
vi) HOC₂H₂
i) C,H5NH,
iv) (C$Hs)₂CO
ii) (C₂Hs)3N
v) (C₂H5)₂CH+
viii) CH,SH
vii) CN
ix) CH₂CH₂CH₂CH₂ Br
b) i) Draw the curly arrow mechanism for the reaction between v) and vii)
x) (CH3)3CBr
ii) of the two C atoms involved do any change their hybridisation? If so, how?
PROBLEM 3
Suggest mechanisms for these eliminations. Why does the first give a mixture
and the second a single product?
OH
OH
H₂PO4
heat
X³
OH
48% HBr
heat
64% yield, 4:1 ratio
Chapter F Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
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