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SOLUTIONS FOR ALKYL HALIDES: NUCLEOPHILIC SUBSTITUTION AND ELIMINATION
From Chapter 6 of Solutions Manual for Organic Chemistry, Eighth Edition. Leroy G. Wade, Jr., Jan W. Simek. Copyright © 2013 by Pearson Education, Inc. 
All rights reserved.
Cl
F
CH2FH
H
I
C HI
IBr
Br
C
Br
Br Br
BrH
C II
H
1 In problems like part (a), draw out the whole structure to detect double bonds:
(a) vinyl halide
(d) alkyl halide
2 (a) (b) (c) (d) (e)
(c) alkyl halide
(f) aryl halide
(g)
(b) alkyl halide
(e) vinyl halide
(f) (h)
or (CH3)3CCl
Br
3 IUPAC name; common name; degree of halogen-bearing carbon
(a) 1-chloro-2-methylpropane; isobutyl chloride; 1° halide
(b) 2-bromo-2-methylpropane; tert-butyl bromide; 3° halide
(c) 1-chloro-2-methylbutane; no common name; 1° halide
(d) 4-fluoro-1,1-dimethylcyclohexane; no common name; 2° halide
(e) 4-bromo-3-methylheptane; no common name; 2° halide
(f) cis-1-bromo-2-chlorocyclobutane; no common name; both 2° halides; 
also correct is (1R,2S)-1-bromo-2-chlorocyclobutane
You may have drawn the other 
enantiomer. Either is correct.
Cl
Cl
Cl
Cl
Cl Cl
Cl
ClCl
Cl
ClCl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
Cl
ClClO
Cl
Cl
Cl
Cl
Cl
O Cl Cl
Cl
Cl
Cl
Cl
Cl
Cl
Kepone®
4
Chlordane®
H
F
structure
in part (a)
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