OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
Chapter 10 – Organohalides
Solutions to Problems
10.1 The rules that were given for naming alkanes in Section 3.4 are used for alkyl halides. A
halogen is treated the same as an alkyl substituent but is named as a halo group.
(a) (b)
(c) (d)
(e) (f)
10.2
(a) (b)
(c) (d)
(e) (f)
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, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
10.3
Chlorination at sites b and e yields achiral products. The products of chlorination at sites
a, c and d are chiral; each product is formed as a racemic mixture of enantiomers.
10.4
Type of –H a b c d
Number of –H of each 6 1 2 3
type
Relative reactivity 1.0 5.0 3.5 1.0
Number times reactivity 6.0 5.0 7.0 3.0
Percent chlorination 29% 24% 33% 14%
11/16/2023 2
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
10.5
10.6
Product B is favored because the reaction at the primary end of the allylic radical yields
a product with a trisubstituted double bond.
10.7 (a)
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Chapter 10 – Organohalides
Solutions to Problems
10.1 The rules that were given for naming alkanes in Section 3.4 are used for alkyl halides. A
halogen is treated the same as an alkyl substituent but is named as a halo group.
(a) (b)
(c) (d)
(e) (f)
10.2
(a) (b)
(c) (d)
(e) (f)
1 8/9/2023
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
10.3
Chlorination at sites b and e yields achiral products. The products of chlorination at sites
a, c and d are chiral; each product is formed as a racemic mixture of enantiomers.
10.4
Type of –H a b c d
Number of –H of each 6 1 2 3
type
Relative reactivity 1.0 5.0 3.5 1.0
Number times reactivity 6.0 5.0 7.0 3.0
Percent chlorination 29% 24% 33% 14%
11/16/2023 2
, OpenStax Organic Chemistry: A Tenth Edition Student Solutions Manual
10.5
10.6
Product B is favored because the reaction at the primary end of the allylic radical yields
a product with a trisubstituted double bond.
10.7 (a)
3 11/16/2023
