Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 6: Problem 81

An organic compound (A) \(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{NO}\) on hydrolysis gives (B) which forms a silver mirror with Tollens' reagent and (C) which fails to dissolve in alkali after reacting with Hinsberg's reagent. (A) is (a) N,N-dimethyl formamide. (b) N-Ethyl formamide (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CONH}_{2}\) (d) N-methyl acetamide

Short Answer

Expert verified
Answer: (b) N-Ethyl formamide.

Step by step solution

01

List the given compounds and their molecular formulas

Here are the molecular formulas for each option: (a) N,N-dimethyl formamide: \(\mathrm{HCON(CH}_{3})_{2}\) (b) N-Ethyl formamide: \(\mathrm{HCONHCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CONH}_{2}\): \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONH}_{2}\) (d) N-methyl acetamide: \(\mathrm{CH}_{3} \mathrm{CONHCH}_{3}\) All have the proper molecular formula (\(\mathrm{C}_{3} \mathrm{H}_{7} \mathrm{NO}\)), so we have to look at their hydrolysis products.
02

Determine products of hydrolysis for each compound

For each compound, determine the products of hydrolysis: (a) N,N-dimethyl formamide: \(\mathrm{HCON(CH}_{3})_{2} + \mathrm{H}_{2}\mathrm{O} \rightarrow \mathrm{HCHO} + 2\mathrm{NH(CH}_{3})_{2}\) (b) N-Ethyl formamide: \(\mathrm{HCONHCH}_{2} \mathrm{CH}_{3} + \mathrm{H}_{2}\mathrm{O} \rightarrow \mathrm{HCHO} + \mathrm{NHCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CONH}_{2}\): \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CONH}_{2} + \mathrm{H}_{2}\mathrm{O} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO} + \mathrm{NH}_{3}\) (d) N-methyl acetamide: \(\mathrm{CH}_{3} \mathrm{CONHCH}_{3} + \mathrm{H}_{2}\mathrm{O} \rightarrow \mathrm{CH}_{3} \mathrm{CHO} + \mathrm{NHCH}_{3}\)
03

Identify which hydrolysis products match the given information

Compound (B) should be an aldehyde, and compound (C) should be a secondary amine. Looking at the hydrolysis products from step 2: (a) The product \(\mathrm{HCHO}\) is an aldehyde, but \(\mathrm{NH(CH}_{3})_{2}\) is a tertiary amine, not a secondary amine. (b) The product \(\mathrm{HCHO}\) is an aldehyde, and \(\mathrm{NHCH}_{2} \mathrm{CH}_{3}\) is a secondary amine. This matches the given information. (c) The product \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CHO}\) is an aldehyde, but \(\mathrm{NH}_{3}\) is a primary amine, not a secondary amine. (d) The product \(\mathrm{CH}_{3} \mathrm{CHO}\) is an aldehyde, but \(\mathrm{NHCH}_{3}\) is a primary amine, not a secondary amine.
04

Choose the correct option

Based on the analysis in step 3, the only compound that matches the given information is compound (b) N-Ethyl formamide. Therefore, the correct answer is (b) N-Ethyl formamide.

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 amino acid, if a proton migrates from carboxyl group to amino group, the product is called (a) dipolar ion (b) Zwitterion (c) internal salt (d) all the above

Gabriel phthalimide synthesis is used for the preparation of (a) primary amines (b) secondary amines (c) \(\alpha\) -amino acids (d) both (a) and (c)

The hybridization of nitrogen in aniline is (a) \(s p\) (b) \(\mathrm{sp}^{2}\) (c) \(\mathrm{sp}^{3}\) (d) \(\mathrm{sp}^{3} \mathrm{~d}\)

The pKa values of \(-\mathrm{COOH},-\mathrm{SH}\) and \(-\mathrm{N} \mathrm{H}_{3}\) groups present in the amino acid cysteine are \(1.8,8.2\) and \(10.8\) respectively. The structure of cysteine at a \(\mathrm{pH}=5\) will be

Match the elements of Column I to elements of Column II. There can be single or multiple matches. Column I (a) Coupling reaction (b) Liebermann's nitroso reaction (c) Hinsberg reaction (d) Carbylamine reaction Column II (p) Phenol (q) Aniline (r) N-methylethanamine (s) Tertiary butyl amine
See all solutions

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

Inorganic Chemistry

Read Explanation

Making Measurements

Read Explanation

Organic 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