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Choose the member of each pair that will react faster by

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 23P Chapter 6

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 23P

Choose the member of each pair that will react faster by the SN1 mechanism.

(a) 1-bromopropane or 2-bromopropane

(b) 2-bromo-2-methylbutane or 2-bromo-3-methylbutane

(c) n-propyl bromide or allyl bromide

(d) 1-bromo-2,2-dimethylpropane or 2-bromopropane

(e) 2-iodo-2-methylbutane or tert-butyl chloride

(f) 2-bromo-2-methylbutane or ethyl iodide

Step-by-Step Solution:
Step 1 of 3

Answer :

The structure that can form the more stable carbocation will undergo SN1 mechanism faster

(a) 1-bromopropane or 2-bromopropane

2-Bromopropane will react faster by the SN1 mechanism than 1-bromopropane because secondary alkyl halide while 1-Bromopropane is primary alkyl halide .In general ,secondary alkyl halides are more favourable for SN1 reaction than primary alkyl halides .

(b) 2-bromo-2-methylbutane or 2-bromo-3-methylbutane

2-Bromo-2-methylbutane will form a tertiary carbocation will undergo SN1 mechanism because it is the most stable carbocation and  2-bromo-3-methylbutane forms secondary carbocation which is less stable than tertiary carbocation.

(c) n-propyl bromide or allyl bromide

 n-propyl bromide is not having any resonance structure so the formation of stable carbocation is difficult in this case .whereas allyl bromide is having double bond and probably having resonance structures and forming the stable carbocation and thus it can form SN1 mechanism faster than the n-propyl bromide .

(d) 1-bromo-2,2-dimethylpropane or 2-bromopropane

Step 2 of 3

Chapter 6, Problem 23P is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

This textbook survival guide was created for the textbook: Organic Chemistry, edition: 8. Since the solution to 23P from 6 chapter was answered, more than 1900 students have viewed the full step-by-step answer. The answer to “Choose the member of each pair that will react faster by the SN1 mechanism.(a) 1-bromopropane or 2-bromopropane(b) 2-bromo-2-methylbutane or 2-bromo-3-methylbutane(c) n-propyl bromide or allyl bromide(d) 1-bromo-2,2-dimethylpropane or 2-bromopropane(e) 2-iodo-2-methylbutane or tert-butyl chloride(f) 2-bromo-2-methylbutane or ethyl iodide” is broken down into a number of easy to follow steps, and 36 words. The full step-by-step solution to problem: 23P from chapter: 6 was answered by , our top Chemistry solution expert on 05/06/17, 06:41PM. Organic Chemistry was written by and is associated to the ISBN: 9780321768414. This full solution covers the following key subjects: bromo, methylbutane, bromopropane, bromide, dimethylpropane. This expansive textbook survival guide covers 25 chapters, and 1336 solutions.

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