Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 18: Q6P (page 929)

Show how you would synthesize each compound from starting materials containing no more than six carbon atoms.

(a)

(b)

(c)

Short Answer

Expert verified

(a)

(b)

(c)

Step by step solution

01

Reaction of Carbonyl Compound

Carbonyl compounds (aldehydes and ketones) reacts with RMgX to form alcohols as the major product. Aldehyde gives secondary alcohols whereas ketone gives tertiary alcohols.

02

Synthetic methodology

(a) 1-bromo cyclohexane is first treated with magnesium in the presence of ether to form grignard reagent (cyclohexylmagnesium bromide). The so formed grignard reagent undergoes hydrolysis to form an alcohol. Again, the alcohol is oxidised by PCC to form the target compound. The corresponding reactions are shown below.

(b) Benzene can be converted to propiophenone by Friedel Crafts acylation reaction. In this reaction, benzene combine with propanoyl chloride in the presence of Lewis acid AlCl3 to form an aromatic ketone (propiophenone). The corresponding reaction is shown.

(c) 1-bromocyclopentane is first treated with magnesium in the presence of ether to form grignard reagent (cyclopentylmagnesium bromide). The so formed grignard reagent undergoes treatment with epoxide and subsequent hydrolysis to form an alcohol. Again, the alcohol is oxidised by PCC to form the target compound. The corresponding reactions are 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.

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

Predict the major products of the following reactions:

(a) (b)

(c) (d)

Show how you would accomplish the following syntheses efficiently and in good yield. You may use any necessary reagents.

(a)acetaldehyde→lacticacid,CH3CH(OH)COOH

(b)

(c)

(d)

(e)

(f)

(g)

Predict the products of the following reactions.

(a) CH3CH2CH2C≡N+CH3CH2MgBr,thenH3O+

(b) CH3CH2CH2C≡N+DIBAL-H,thenH3O+

(c) Benzylchloride+potassiumcyanide

(d) Productofc+cyclopentylmagnesiumchloride,thenacidichydrolysis

(e) Productofc+DIBAL-H,thenhydrolysis

Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration:

CH3COCH2Br BrCH2CHO      CH2O      CH3COCH3      CH3CHO

Both NaBH4 and NaBD4 are commercially available, and D2O is common and inexpensive. Show how you would synthesize the following labelled compounds, starting with propanone.
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

Read Explanation

Organic Chemistry

Read Explanation

Making Measurements

Read Explanation

Inorganic 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