Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 11: Q11-70E (page 350)

(S)-2-Butanol slowly racemizes on standing in dilute sulfuric acid. Explain.

Short Answer

Expert verified

Mechanism for the reaction

Step by step solution

01

Secondary alcohol

Since 2-butanol is a secondary alcohol, substitution can occur by either an SN1orSN2route, depending on reaction conditions. Two factors favor aSN1mechanism in this case. The reaction is run under solvolysis (solvent as a nucleophile) conditions in a polar, protic solvent. Dilute acid converts a poor leaving groupOH- into a good leaving groupdata-custom-editor="chemistry" OH2which dissociates easily.

02

Explanation

Initially, there is protonation of the hydroxyl oxygen, which is then followed by a loss of water to form a planar carbocation. Finally, an attack of water from either side of the planar carbocation yields a racemic product.

Mechanism for the reaction

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

Draw all isomers of C4H9Br,name them, and arrange them in order of decreasing reactivity in theSN2reaction:

Question: What stereochemistry do you expect for the alkene obtained by E2 elimination of (1R, 2R)-1,2-dibromo-1,2-diphenylethane? Draw a Newman projection of the reacting conformation.

Which substance in each of the following pairs is more reactive as a nucleophile? Explain.

(a)CH32N-orCH32NH(b) (CH3)3Bor(CH3)3N(c)H2OorH2S

What stereochemistry do you expect for the trisubstituted alkene obtained by E2 elimination of the following alkyl halide on treatment with KOH? (Reddish brown = Br.)

Compound X is optically inactive and has the formulaC16H16Br2. On treatment with strong base, X gives hydrocarbon Y,C16H14. Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment, Z, is an aldehyde with formulaC7H6O. The other fragment is glyoxal,(CHO)2. Write the reactions involved, and suggest structures for X, Y, and Z. What is the stereochemistry of X?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Chemical Analysis

Read Explanation

Physical Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

The Earths Atmosphere

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