Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 6: Problem 46

When phenyl alanine is treated with nitrous acid, the product obtained is (a) 1 -amino-2-phenyl-ethanol (b) 3 -hydroxy- 2 -phenyl-propanoic acid (c) 2 -amino- 1 -phenyl-ethanol (d) 2-hydroxy-3-phenyl-propanoic acid

Short Answer

Expert verified
Answer: 3-hydroxy-2-phenyl-propanoic acid

Step by step solution

01

Identify the structure of phenyl alanine

Phenyl alanine is an α-amino acid with a benzyl side chain. Its structure can be represented as follows: HOOC-CH(NH₂)-CH₂-C₆H₅ (COOH and NH₂ represent the carboxyl and amino groups, respectively, and C₆H₅ represents the phenyl group)
02

Understand nitrous acid reaction

Nitrous acid (HONO) is a weak and unstable acid. It reacts with primary amines, such as the amino group in phenyl alanine, to form an intermediate diazonium salt. The diazonium salt is highly reactive and reacts with water to form a hydroxyl group (-OH) at the same position where the amino group (-NH₂) was initially present.
03

Determine the product structure

Based on the reaction mechanism of nitrous acid with primary amines, we know that the amino group (-NH₂) of phenyl alanine will be replaced with a hydroxyl group (-OH). By doing this, the product formed will have the following structure: HOOC-CH(OH)-CH₂-C₆H₅
04

Match the product structure with the given options

Now, let's match the product structure we obtained with the given options. (a) 1 -amino-2-phenyl-ethanol is incorrect because the amino group has not been replaced with a hydroxyl group. (b) 3 -hydroxy- 2 -phenyl-propanoic acid is the correct answer, as it represents the structure of the product we obtained in Step 3 (HOOC-CH(OH)-CH₂-C₆H₅). (c) 2 -amino- 1 -phenyl-ethanol is incorrect because the amino group has not been replaced with a hydroxyl group. (d) 2-hydroxy-3-phenyl-propanoic acid is incorrect because the hydroxyl group is attached to the wrong carbon atom. Thus, the correct answer is (b) 3 -hydroxy- 2 -phenyl-propanoic acid.

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

A series of offsets were taken at \(5 \mathrm{~m}\) intervals from a chain line to a curved edge. 1.50. \(1.66,2.25,2.80,1.75,1.95,0\) Calculate the area between the chain line to a curved edge by the Simpson's rule and the trapezoidal rule.

Explain the principle of chain survey.

Para toluidine is treated with \(\mathrm{HNO}_{2}\) at ice cold conditions and then boiled with water. The final product obtained is (a) anthranilic acid (b) \(\mathrm{p}\) -cresol (c) toluic acid (d) phenol

The major product (A) is

For an amino acid \(\mathrm{R}\) is an alkyl group. It is made into a solution with water. To the solution a few drops of dil. HCl are added and the solution is electrolysed. Which of the following would happen? (a) The amino acid becomes an anion. (b) The protonated amino acid moves to the cathode. (c) The protonated amino acid moves to the anode. (d) The amino acid decomposes.
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Analysis

Read Explanation

Kinetics

Read Explanation

Making Measurements

Read Explanation

Inorganic Chemistry

Read Explanation

Chemistry Branches

Read Explanation

The Earths Atmosphere

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