Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 10: Problem 106

The most comanon preparation of thiols, RSH1, depends on the high nucleophilicity of the hydrosulfide ion, 115 (Section 9.3E). Sodium hydrosulfide is prepared by bubbling \(\mathrm{H}_{2} \mathrm{~S}\) through a solution of \(\mathrm{NaOH}\) in water or aqueous ethanol. Reaction of HIS' with a haloalkane gives a thiol.

Short Answer

Expert verified
Question: Explain the process of preparing thiols using sodium hydrosulfide and a haloalkane. Answer: The process involves three main steps: (1) preparation of sodium hydrosulfide by reacting hydrogen sulfide gas with sodium hydroxide, (2) reacting the hydrosulfide ion (HS-) with a haloalkane to form a thiol (RSH), and (3) isolating and purifying the thiol product from other reaction products.

Step by step solution

01

Preparation of Sodium Hydrosulfide

Sodium hydrosulfide (\(\mathrm{NaHS}\)) is prepared by bubbling hydrogen sulfide gas (\(\mathrm{H}_{2}\mathrm{S}\)) through a solution of sodium hydroxide (\(\mathrm{NaOH}\)) in water or aqueous ethanol. The reaction can be represented as follows: \(\mathrm{H}_{2} \mathrm{S} + \mathrm{NaOH} \longrightarrow \mathrm{NaHS} + \mathrm{H}_{2}\mathrm{O}\)
02

Reaction of Hydrosulfide Ion with a Haloalkane

The hydrosulfide ion (HS-) is a good nucleophile. It reacts with a haloalkane (RX, where R is an alkyl group and X is a halogen atom) to give a thiol (RSH). The reaction can be represented as below: \(\mathrm{NaHS}(\mathrm{HS^{-}}) + \mathrm{R}\mathrm{X} \longrightarrow \mathrm{R}\mathrm{SH} + \mathrm{NaX}\)
03

Isolate the Thiol Product

The thiol product (RSH) can be separated from the other product, sodium halide (NaX), by using techniques such as extraction or filtration, depending on the specific properties of the products. Once isolated, purification methods such as recrystallization or distillation can be used to obtain pure thiol compound. These are the essential steps in the preparation of thiols using sodium hydrosulfide and a haloalkane.

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

Break bonds to give stable molecules or ions. Redistribution of valence electrons within the cyclic periodate gives \(\mathrm{HIO}_{3}\) and two carbomyl groups. A result of this electron redistribution is an oxidation of the organic component and a reduction of the iodine-containing component. \(\mathrm{HUO}_{3}\) (lodic acid)

The form of Cr(VT) most commonly used for oxidation of a primary alcohol to an aldehyde is prepared by dissolving \(\mathrm{CrO}_{3}\) in aqueous \(\mathrm{HCl}\) and adding pyridine to precipitate pyridinium chlorochromate \((\mathrm{PCC})\) as a solid. Pyridine Pyridinum chlorochromate (PCC)

Hydrogen sulfide is much more acidic than water.

Primary alcohols are oxidized by aqueous \(\mathrm{H}_{2}\) CrO \(\mathrm{O}_{4}\) to give carboxylic acids in a process that involves initial aldehyde formation, followed by conversion to an aldehyde hydirate that is further cxidized to the casboxylic acid.

Draw the product of treating each alcohol with \(\mathrm{PCC}\). (a) M-Mexanol (b) 2.Mexanol (c) Cyclohexanol
See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Organic Chemistry

Read Explanation

The Earths Atmosphere

Read Explanation

Making Measurements

Read Explanation

Physical Chemistry

Read Explanation

Chemical Analysis

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