/*! 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} Q52P Compound A is an optically activ... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 11: Q52P (page 589)

Compound A is an optically active alcohol. Treatment with chromic acid converts A into a ketone, B. In a separate reaction, A is treated with PBr3, converting A into compound C. Compound C is purified, and then it is allowed to react with magnesium in ether to give a Grignard reagent, D. Compound B is added to the resulting solution of the Grignard reagent. After hydrolysis of the initial product (E), this solution is found to contain 3,4 dimethylhexan-3-ol. Propose structures for compounds A, B, C, D, and E.

Short Answer

Expert verified

The compound that bears one or more hydroxide groups (OH) is called alcohol. The alcohols have very large applications in organic synthesis. It has wide applications in perfume and cleaning agents.

Step by step solution

01

About alcohol

The compound that bears one or more hydroxide groups (OH) is called alcohol. The alcohols have very large applications in organic synthesis. It has wide applications in perfume and cleaning agents.

02

About the reaction

Compound A is butan-2-ol. When it is treated with PB3, it forms 2-bromobutane. So the compound C is 2-bromobutane. When it is treated with magnesium metal in the ether it forms sec-butylmagnesium bromide. So, compound D is sec-butylmagnesium bromide.

03

About the reaction

When butan-2-ol is treated with NaOCl/HOAc it gives butan-2-one. So, compound B is butan-2-one. When sec-butylmagnesium and butan-2-one react together, there will be the formation of magnesium 3,4-dimethylhexan-3-olate bromide. So, compound E is magnesium 3,4-dimethylhexan-3-olate bromide. When it is acidified, 3,4-dimethylhexan-3-ol is formed. So, the final compound is 3,4-dimethylhexan-3-ol. The reaction is shown below.

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

A student wanted to use the Williamson ether synthesis to make (R)-2-ethoxybutane. He remembered that the Williamson synthesis involves an SN2 displacement, which takes place with inversion of configuration. He ordered a bottle of (S)-butan-2-ol for his chiral starting material. He also remembered that the SN2goes best on primary halides and tosylates, so he made ethyl tosylate and sodium (S)-but-2-oxide. After warming these reagents together, he obtained an excellent yield of 2-ethoxybutane.

(a) What enantiomer of 2-ethoxybutane did he obtain? Explain how this enantiomer results from the SN2 reaction of ethyl tosylate with sodium (S)-but-2-oxide.

(b) What would have been the best synthesis of (R)-2-ethoxybutane?

(c) How can this student convert the rest of his bottle of (S)-butan-2-ol to (R)-2-ethoxybutane?

Two products are observed in the following reaction.

(a) Suggest a mechanism to explain how these two products are formed.

(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in

this case.

Propose a mechanism for each reaction.

(a)

(b)

Unknown Q is determined to have a molecular formula of C6H12O. Q is not optically active, and passing it through a chiral column does not separate it into enantiomers. Q does not react with Br2, nor with cold, dilute KMnO4 , nor does it take up H2under catalytic hydrogenation. Heating of Q with H2SO4 gives product R, of formula C6H10, which can be separated into enantiomers. Ozonolysis of a single enantiomer of R produces S, an acyclic, optically active ketoaldehyde of formula C6H10O2. Propose structures for compounds Q, R, and S, and show how your structures would react appropriately to give these results.

Show how you would convert (S)-heptan-2-ol to

(a) (S)-2-chloroheptane.

(b) (R)-2-bromoheptane.

(c) (R)-heptan-2-ol.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Chemistry Branches

Read Explanation

Nuclear Chemistry

Read Explanation

Physical Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Kinetics

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.