Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 12: Q22-60E (page 354)

The following synthetic routes are incorrect. What is wrong with each?

Short Answer

Expert verified
  1. The reagent path is incorrect.
  2. Aryl halides cannot participate in SN2 reactions.
  3. The product formed is incorrect.

Step by step solution

01

 Step 1: Reaction (a)

The synthetic route for reaction (a) is wrong.

The given reagents are used in this reaction to carry out bromination for the carbonyl compound. Esters do not undergo bromination with the given reagents.

02

Reaction (b)

The synthetic route for reaction (b) is wrong.

In this reaction, an anion forms an anion of a proton from the reactant (diethyl-2-methyl malonate) by the given base.

In the second step, the anion will attack the phenyl bromide, which is impossible. The nucleophilic attack is impossible on aryl halides because of the double bond between carbon and halide.

03

Reaction (c)

The synthetic route for the reaction (c) is wrong.

The correct sequence and the final product for the given reaction is,

Product formed in reaction (c)

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

In light of the nitrogen rule mentioned in Problem 12-17, what is themolecular formula of pyridine, M+=79?

Propose structures for compounds that fit the following mass-spectraldata:

(a) A hydrocarbon with M+= 132

(b) A hydrocarbon with M+=166

(c) A hydrocarbon with M+= 84

Question: Where might the following compounds have IR absorptions?

Propose structures for simple molecules that contain the following functional groups:

(a)Alcohol (b)Aromatic ring (c)Carboxylic acid (d)Amine (e)Both ketone and amine

(f) Two double bonds

Question: Ketones undergo a reduction when treated with sodium borohydride, NaBH4.What is the structure of the compound produced by reactionof 2-butanone with NaBH4 if it has an IR absorption at 3400cm-1andM+=74in the mass spectrum?
See all solutions

Recommended explanations on Chemistry Textbooks

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Inorganic Chemistry

Read Explanation

Chemical Analysis

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