Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 22: 6P (page 868)

Why can’t 1-methylcyclohexanol be prepared from a carbonyl compound by reduction?

Short Answer

Expert verified

Answer

In 1-methyl cyclohexanol, tertiary alcohol is present, hence it can’t be reduced from any carbonyl compound.

Step by step solution

01

Step-by-Step Solution Step 1: Function of metal hydrides

Metal hydrides such as sodium borohydride and lithium aluminium hydride are strong reducing agents that can reduce an aldehyde into primary alcohol and a ketone into secondary alcohol.

These are as shown below:

02

Structure of 1-methylcyclohexanol

The structure of 1-methylcyclohexanol has a tertiary alcoholic group, which is shown below:

03

Observation of the structure

The structure contains a tertiary alcohol group where no α-hydrogen is present. Hence, it cannot be reduced by any carbonyl group, as the valency of the carbonyl group exceeds its valency of 4.

Based on the explanations, in the case of 1-methyl cyclohexanol, tertiary alcohol is present. Hence, it can’t be reduced from any carbonyl compound.

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

Which carbon is most electrophilic in Compound Y? Explain your choice.

Fill in the lettered products (A–D) in the synthesis of (R)-isoproterenol, a drug that increases heart rate and dilates lung passages.

Question: Draw the three possible resonance structures for an acid bromide, . Then, using the pKa values in Appendix A, decide if RCOBr is more or less stabilized by resonance than a carboxylic acid (RCOOH).

What aldehyde or ketone is needed to prepare each alcohol by metal hydride reduction?
  1. What orbitals are used to form the indicated bonds in α-sinensal?
  2. In what type of orbitals do the lone pairs on Oreside?
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Kinetics

Read Explanation

Nuclear Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Physical Chemistry

Read Explanation

Chemical Reactions

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