Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 27: Problem 52

How would you synthesize ( \(R\) )-2-butanamine from (S)-2-butanol?

Short Answer

Expert verified
The synthesis of (R)-2-butanamine from (S)-2-butanol involves three steps: oxidation of the alcohol to the carboxylic acid using an oxidizing agent, reaction of the acid with ammonia to form an amine, and inversion of the stereochemistry to obtain the R isomer.

Step by step solution

01

Oxidation of Alcohol to Carboxylic Acid

Firstly, (S)-2-butanol is converted into 2-butanoic acid. This can be achieved by oxidizing the alcohol with a strong oxidizing agent such as KMnO4 (Potassium permanganate) or Na2Cr2O7 (Sodium dichromate). The reaction proceeds with retention of configuration. The general formula for this reaction is as follows: ROH (alcohol) + [O] (oxidizing agent) -> RCOOH (carboxylic acid).
02

Conversion of Carboxylic Acid to Amine

Next, the 2-butanoic acid is converted to an amine. This is accomplished by heating the acid with ammonia (NH3) in a process known as an amide formation. The carboxylic acid first reacts with the ammonia to form an amide and water. Water is then removed in the next step by heating, which forces the reaction to proceed in the forward direction, leading to the amine formation.
03

Stereochemical Inversion

The product from the previous reaction is (S)-2-butanamine. However, the question asks to synthesize (R)-2-butanamine, thus requiring inversion of stereochemistry. To accomplish this, we react the amine with a chiral acid to form a salt. The salt is then treated with base to give the amine, but now in the R configuration. This method allows for inversion of stereochemistry without changing the overall functionality and structure of the molecule.

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

How would you synthesize \((E)\) - and \((Z)\) -3-heptene from acetylene and any other chemicals?

The iodide ion cannot displace the \(-\mathrm{OH}\) group in ethanol, but excess HI will react to produce ethyl iodide. Explain.

Answer the following questions for this E1 reaction: $$\begin{array}{c} \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br}+\mathrm{CH}_{3} \mathrm{OH} \longrightarrow \mathrm{CH}_{3} \mathrm{CH}=\mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}+\mathrm{Br}^{-}+\mathrm{CH}_{3} \mathrm{OH}_{2}^{+} \end{array}$$ (a) What is the rate expression for the reaction? (b) Draw the reaction profile for the reaction. Label all parts. Assume that the products are lower in energy than the reactants. (c) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br} ?\) (d) What is the effect on the rate of the reaction of doubling the concentration of \(\mathrm{CH}_{3} \mathrm{OH} ?\)

What is major product expected from the monobromination of 2,2,3 -trimethylpentane?

Draw the structures of the products of each of the following reactions: (a) propene + hydrogen (Pt, heat) (b) 2 -butanol \(+\) heat (in the presence of sulfuric acid)
See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Kinetics

Read Explanation

Physical Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Making Measurements

Read Explanation

Nuclear 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