Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 11: Q11-71E (page 350)

The reaction of HBr with (R)-3-methyl-3-hexanol leads to racemic 3-Bromo-3-methyl hexane. Explain.

Short Answer

Expert verified

Formation of carbocation

Formation of the desired product

Step by step solution

01

Tertiary alcohol

Whenever a tertiary alcohol is treated with a strong acid, a carbocation intermediate is formed.

Formation of carbocation

This carbocation is planar due to the empty p-orbital of the carbocation carbon. Moreover, the tetrahedral chirality that was present in the starting material was lost.

02

Explanation

The chiral starting material goes through an achiral intermediate, such as a carbocation, and the stereochemical information is destroyed. Hence, treatment of 3 -methyl -3-hexanol with HBr forms a carbocation intermediate because 3-methyl-3-hexanol is a tertiary alcohol. This intermediate loses all stereochemical information so the product is racemized.

Formation of the desired product

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.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

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

Propose a mechanism for the following reaction, an important step in the laboratory synthesis of proteins:

Propose a structure for an alkyl halide that gives only (E)-3-methyl-2-phenyl-2-pentene on E2elimination. Make sure you indicate the stereochemistry.

Rank the following compounds in order of their expected reactivity toward SN2reaction:

CH3Br,CH3OTos,CH33CCl,CH32CHCl

What product(s) would you expect from reaction of (S)-3-chloro-3-methyloctane with acetic acid? Show the stereochemistry of both reactant and product

Which reaction in each of the following pairs would you expect to be faster?

(c) TheSN2displacement on 2-bromopropane by CH3CH2O-or byCN-
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Chemistry Branches

Read Explanation

The Earths Atmosphere

Read Explanation

Physical Chemistry

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.

Sign-up for free