Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 18: 18-31P (page 677)

What steps are needed to convert benzene into p-isobutyl acetophenone, a synthetic intermediate used in the synthesis of the anti-inflammatory agent ibuprofen.

Short Answer

Expert verified

Steps in the synthesis of Ibuprofen

Step by step solution

01

Clemmensen reduction

Clemmensen reduction is the reduction of carbonyl groups in aldehydes and ketones to methylene group.

The reaction is done with zinc amalgam and hydrochloric acid.

02

Steps in converting benzene into p-isobutyl acetophenone

Benzene is converted into p-isobutyl acetophenone by Friedel-craft's acylation followed by Clemmensen reduction (Zn (Hg) + HCl).

The reduced product is again subjected to Friedel-craft's acylation to get p-isobutyl acetophenone.

03

Steps in converting p-isobutyl acetophenone to ibuprofen

  • Sulfur ylide reacts with carbonyl compound and forms epoxide.
  • Epoxide ring opening is followed by hydride transfer to form aldehyde.
  • Aldehyde undergoes oxidation to form ibuprofen.

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

Question: Friedel-Crafts alkylation of benzene with (R)-2-chlorobutane and AlCl3 affords sec-butylbenzene.

  1. How many stereogenic centers are present in the product?
  2. Would you expect the product to exhibit optical activity? Explain, with reference to the mechanism.

Question: Draw a stepwise mechanism for the following reaction, which results in the synthesis of bisphenol F (R = H), an additive used in a variety of packaging materials. Bisphenol F is related to BPA (bisphenol A, R = ), a reagent used to harden some plastics, now removed from certain baby products because of its estrogen-like activity that can disrupt endocrine pathways.

Question: Devise a synthesis of each compound from phenol and any other organic or inorganic reagents.

a.Draw resonance structures for the carbocation formed after loss of a leaving group from phytyl diphosphate.

b. Draw the two-step mechanism for Friedel–Crafts alkylation of 1,2-dihydroxynaphthoic acid with this carbocation to form X.

Question: Although two products (A and B) are possible when naphthalene undergoes electrophilic aromatic substitution, only A is formed. Draw resonance structures for the intermediate carbocation to explain why this is observed.
See all solutions

Recommended explanations on Chemistry Textbooks

Nuclear Chemistry

Read Explanation

Physical Chemistry

Read Explanation

Making Measurements

Read Explanation

Kinetics

Read Explanation

Chemistry Branches

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