/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q7-21P On treatment with HBr, vinylcycl... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 7: Q7-21P (page 219)

On treatment with HBr, vinylcyclohexane undergoes addition and rearrangement to yield 1-bromo-1-ethylcyclohexane. Using curved arrows, propose a mechanism to account for this result.

Short Answer

Expert verified

If the electrophilic addition reaction happens in a single step, it is difficult to explain the rearrangement reaction. Those rearrangement reactions happening in multiple steps can be explained easily.

Step by step solution

01

Step-by-Step solutionStep 1: Electrophilic addition: Carbocation rearrangement

If the electrophilic addition reaction happens in a single step, it is difficult to explain the rearrangement reaction. Those rearrangement reactions happening in multiple steps can be explained easily.

02

Mechanism for the reaction of vinyl cyclohexane with HBr

In the first step, the double bond of the vinylcyclohexane attacks the HBr to yield a secondary carbocation intermediate, expelling a bromide ion. In the next step, the secondary carbocation generated rearranges to a tertiary carbocation by a hydride shift from the adjacent carbon. In the final step, the bromide ion reacts with the tertiary carbocation to generate 1-bromo-1-ethylcyclohexane.

The mechanism can be given as:

Mechanism of the reaction of vinylcyclohexane with HBr

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

Assign E or Z configuration to the following alkenes:

Predict the products of the following reactions:

tert-Butyl [RCO2C(CH3)3] esters are converted into carboxylic acids [RC02H] by reaction with trifluoroacetic acid, a reaction useful in protein synthesis (Section 26-7). Assign E, Z designation to the double bonds of both reactant and product in the following scheme, and explain why there is an apparent change in double-bond stereochemistry:

Vinylcyclopropane reacts with HBr to yield a rearranged alkyl bromide. Follow the flow of electrons as represented by the curved arrows, show the structure of the carbocation intermediate in brackets, and show the structure of the final product.

Sketch the transition-state structures involved in the reaction of HBr with 1-pentene (Problem 7-69). Tell whether each structure resembles reactant or product.
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Chemical Analysis

Read Explanation

Making Measurements

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Chemistry Branches

Read Explanation

Organic Chemistry

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.