What is a good method (an easy method that gives a pure product in good yield) for carrying out the following transformation? $$ \mathrm{R}-\mathrm{CH}_{2}-\mathrm{Br} \rightarrow \mathrm{R}-\mathrm{CH}_{2}-\mathrm{NH}_{2} $$

Short Answer

Expert verified
To carry out the transformation of an alkyl bromide (R-CH2-Br) to an amine (R-CH2-NH2) efficiently, perform a nucleophilic substitution reaction using excess ammonia as the nucleophile. Optimize the reaction conditions by maintaining a low temperature (around 0°C) and using an inert atmosphere (such as nitrogen or argon). Once the reaction is complete, isolate the amine product by evaporating the excess ammonia, extracting the product with a suitable solvent, and drying the organic layer. This method will provide a good yield and a pure product.

Step by step solution

01

1. Identify the Reaction Type

To transform an alkyl bromide (R-CH2-Br) into an amine (R-CH2-NH2), we need to replace the bromine atom (Br) with an amine group (NH2). This type of reaction is called nucleophilic substitution, as the nucleophile (the amine group) replaces the leaving group (the bromine atom) in the starting molecule.
02

2. Choose an Appropriate Reagent

A suitable nucleophile to use in this reaction is ammonia (NH3). We will be using excess ammonia in a solution, as it will not only serve as the nucleophile but also act as a solvent for the reaction.
03

3. Reaction Conditions

To obtain a good yield and pure product, it is important to ensure that the reaction conditions are optimal. In this case, carry out the reaction at low temperature (around 0°C) and under an inert atmosphere (such as nitrogen or argon) to prevent side reactions or decomposition of the reactants and product.
04

4. Perform the Reaction

Combine the alkyl bromide (R-CH2-Br) with excess ammonia in a suitable vessel under an inert atmosphere, and slowly cool the mixture to 0°C. Allow the reaction to proceed until it is complete, which could take several hours. You can monitor the progress by using techniques like thin-layer chromatography (TLC) or nuclear magnetic resonance (NMR).
05

5. Isolate the Product

Once the reaction is complete, you can isolate the desired amine product (R-CH2-NH2). First, remove the excess ammonia by evaporating it off under reduced pressure. Next, extract the product using an appropriate solvent (such as ethyl acetate) and separate the organic layer. Finally, dry the organic layer with a drying agent (such as magnesium sulfate), and evaporate the solvent under reduced pressure to obtain the pure amine product (R-CH2-NH2). In summary, the reaction can be carried out efficiently by using a nucleophilic substitution reaction with excess ammonia as the nucleophile, under low temperature and inert atmosphere conditions. Following this procedure will result in the desired transformation with a good yield and purity of the product.

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.

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

See all solutions

Recommended explanations on Chemistry Textbooks

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