(e) Br- (g)

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter11: Ethers, Epoxides, And Sulfides
Section: Chapter Questions
Problem 11.45P: Using your reaction roadmap as a guide, show how to convert cyclohexanol into racemic...
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Identify the reagents that vou would use to accomplish each of the following transformation:
Transcribed Image Text:Identify the reagents that vou would use to accomplish each of the following transformation:
(e)
Br-
(g)
Transcribed Image Text:(e) Br- (g)
Expert Solution
Step 1-Introduction

The addition reaction of an alkene with a hydrogen halide to furnish the haloalkane is termed as the hydrohalogenation reaction. In this reaction, the sp2 hybridized molecule is altered into the sp3 hybridized molecule at the point of hydrogen halide attack (Markovnikov's rule). The reaction proceeds via the formation of the carbocation intermediate. The higher the stability of the carbocation, the greater will the ease of its formation. The stability order of the carbocation: tertiary>secondary>primary (due to the hyperconjugation effects). The reaction of an alkyl halide with a strong base leads to the formation of an alkene. The reaction is termed as the elimination reaction. Based on the reaction conditions and the concentration of the nature of the alkyl halide, the pathway of the elimination reaction can be E2 or E1.  

Step 2-Predicting the reaction conditions

e) HCl

The reaction of the alkene with HCl initially involves the electrophilic addition of the H+ ion to the alkene to furnish the tertiary carbocation. Then the nucleophilic addition of the Cl- ion to the carbocation furnishes the addition product, a tertiary alkyl halide. 

g) NaOCH3/CH3OH

When the secondary alkyl bromide is treated with a strong base NaOCH3/CH3OH, the base abstracts the products from the adjacent carbon atom in such a way that the more stable alkene is formed. According to Zaitsev's rule, the more substituted alkene is found to have greater stability than the less substituted alkene. Since the alkene product obtained is tetrasubstituted, it is the most stable alkene and hence the unsubstituted alkene product formation is neglected. 

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