Logout Open In App
Open In App
Warning: foreach() argument must be of type array|object, bool given in /var/www/html/web/app/themes/studypress-core-theme/template-parts/header/mobile-offcanvas.php on line 20

Chapter 9: Q31P (page 494)

Question:The application box in the margin of page 473 states, “The addition of an acetylide ion to a carbonyl group is used in the synthesis of ethchlorvynol, a drug used to cause drowsiness and induce sleep.” Show how you would accomplish this synthesis from acetylene and a carbonyl compound.

ethchlorvynol

Short Answer

Expert verified

Synthesis of ethchlorovynol

Step by step solution

01

 Step-by-Step Solution Step 1: About ethchlorovynol

The sedative medication developed by the scientist Pfizer is ethchlorovynol. This drug is used for the treatment of insomnia. This drug is a member of carbinol that has a simpler structure.

02

About the structure of ethchlorovynol

The IUPAC name for ethchlorovynol is 1-chloro-3-ethylpent-1-en-4-yn-3-ol. This compound has one triple bond. The functional groups present in this compound are alcohol and chloro group.

03

Synthesis of ethchlorovynol

The (Z)-1-chloropent-1-en-3-one is treated with ethynide in the presence of sodium amide. On treatment with acid, ethchlorovynol is obtained. The mechanism is given below.

Synthesis of ethchlorovynol

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

The following functional group interchange is a useful synthesis of aldehydes.

(a)What reagents were used in this chapter for this transformation? Give an example to illustrate this method.

(b)This functional group interchange can also be accomplished using the following sequence.

Propose mechanisms from these steps.

(c) Explain why a nucleophilic reagent such as ethoxide adds to an alkyne more easily than it adds to an alkene.

The boiling points of hex-1-ene (64 °C) and hex-1-yne (71 °C) are sufficiently close that it is difficult to achieve a clean separation by distillation. Show how you might use the acidity of hex-1-yne to remove the last trace of it from a sample of hex-1-ene.

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?

Question: Predict the products of the following acid-base reactions, or indicate if no significant reaction would take place.

(a)H-C≡C-H+NaNH2(b)H-C≡C-H+CH3Li(c)H-C≡C-H+NaOCH3(d)H-C≡C-H+NaOH(e)H-C≡CNa++NaOH(f)H-C≡CNa++H2O(g)H-C≡CNa++H2C=CH2(h)H2C=CH2+NaNH2(i)CH3OH+NaNH2

Show how hex-1-yne might be converted to

(a) 1,2-dichlorohex-1-ene. (b) 1-bromohex-1-ene.

(c) 2-bromohex-1-ene. (d) 1,1,2,2-tetrabromohexane.

(e) 2-bromohexane. (f) 2,2-dibromohexane.
See all solutions

Recommended explanations on Chemistry Textbooks

Kinetics

Read Explanation

Chemistry Branches

Read Explanation

Chemical Analysis

Read Explanation

The Earths Atmosphere

Read Explanation

Ionic and Molecular Compounds

Read Explanation

Physical 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