Primary, secondary and tertiary alcohols may be distinguished by converting them to the corresponding nitroalkanes and then treating with (a) \(\mathrm{NaNO}_{2}\) and dilute \(\mathrm{HCl}\) (b) \(\mathrm{con} \cdot \mathrm{H}_{2} \mathrm{SO}_{4}\) (c) Sn and hydrochloric acid (d) Ammonium hydroxide

Short Answer

Expert verified
Short Answer: To distinguish between primary, secondary, and tertiary alcohols after converting them into nitroalkanes, treat them with ammonium hydroxide. This reaction forms hydroxamic acids, which create different colored complexes upon treatment with ferric chloride, allowing us to differentiate between the different types of alcohols.

Step by step solution

01

Identifying Primary, Secondary, and Tertiary Alcohols

To distinguish between primary, secondary, and tertiary alcohols, one must first understand their structure. Primary alcohols have the hydroxyl group attached to a carbon atom that is only bonded to one other carbon atom. Secondary alcohols have the hydroxyl group attached to a carbon atom that is bonded to two other carbon atoms. Tertiary alcohols have the hydroxyl group attached to a carbon atom that is bonded to three other carbon atoms.
02

Reaction with Nitroalkanes

Primary, secondary, and tertiary alcohols can be converted into their corresponding nitroalkanes by reacting with an inorganic nitrite such as \(\mathrm{NaNO}_{2}\) and dilute \(\mathrm{HCl}\).
03

Treatment with the given reagents

Now let's analyze the reactions of nitroalkanes with the given reagents: (a) \(\mathrm{NaNO}_{2}\) and dilute \(\mathrm{HCl}\): Nitroalkanes would react with \(\mathrm{NaNO}_{2}\) and dilute \(\mathrm{HCl}\) to form alkyl halides. However, this will not show any distinct results as the alkyl halides formed from primary, secondary, and tertiary alcohols would be similar. (b) \(\mathrm{con} \cdot \mathrm{H}_{2} \mathrm{SO}_{4}\): Nitroalkanes do not show any distinguishing reaction with concentrated sulfuric acid and will not result in identifying primary, secondary, and tertiary alcohols. (c) Sn and hydrochloric acid: Nitroalkanes will react with Sn and hydrochloric acid, resulting in the formation of primary, secondary, and tertiary amines. This reaction will also not differentiate between primary, secondary, and tertiary alcohols since the corresponding amines are similar in structure. (d) Ammonium hydroxide: Nitroalkanes will react with ammonium hydroxide to form hydroxamic acids, which can form colored complexes upon treatment with ferric chloride (FeCl3). Primary, secondary, and tertiary alcohols will give rise to hydroxamic acids with different appearances, which can help differentiate between them. Based on the above analysis, the correct answer is:
04

Answer

(d) Ammonium hydroxide

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