/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} Q.61. Question: Devise a synthesis of ... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 12: Q.61. (page 492)

Question: Devise a synthesis of muscalure, the sex pheromone of the common housefly, from acetylene and any other required reagents.

Muscalure

Short Answer

Expert verified

Answer:

Step by step solution

01

Deprotonation

The organic reaction in which a proton is removed from the compound with the help of a strong base such as sodium or potassium hydride is known as a deprotonation reaction.

The acetylene is deprotonated by the strong base sodium hydride to produce sodium acetylide.

Deprotonation of Acetylene

02

Substitution reaction

The strong base sodium acetylide would undergo a substitution reaction with bromononane to replace bromine with the acetylide anion.

Substitution reaction.

03

Deprotonation and substitution

This compound is again treated with another molecule of sodium hydride, followed by bromotridecane, to form a substituted alkyne.

Deprotonation followed by substitution

04

Reduction reaction

The corresponding alkyne is reduced with hydrogen in the presence of Lindlar鈥檚catalyst to form the cis alkene (Z)-9-tricosene.

Reduction of alkyne to alkene

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 91影视!

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

Question: Stearidonic acid (C18H28O2 ) is an unsaturated fatty acid obtained from oils isolated from hemp and blackcurrant (see also Problem 10.11).

a. What fatty acid is formed when Stearidonic acid is hydrogenated with excess H2 and a Pd catalyst?

b. What fatty acids are formed when stearidonic acid is hydrogenated with one equivalent of H2 and a Pd catalyst?

c. Draw the structure of a possible product formed when stearidonic acid is hydrogenated with one equivalent of H2 and a Pd catalyst, and one double bond is isomerized to a trans isomer.

d. How do the melting points of the following fatty acids compare: stearidonic acid; one of the products formed in part (b); the product drawn in part (c)?

Question: Match each alkene to its heat of hydrogenation.Alkenes: 3-methylbut-1-ene, 2-methylbut-1-ene, 2-methylbut-2-ene 鈭�H掳(hydrogenation) kJ/mol: 鈥�119, 鈥�127, 鈥�112

Question: Draw the organic products in each of the following reactions.

a.

b.

c.

d.

Question: Draw a stepwise mechanism for the following reaction.

Question: Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3+H2O. Explain how these reactions illustrate that syndihydroxylation is stereospecific.

See all solutions

Recommended explanations on Chemistry Textbooks

Inorganic Chemistry

Read Explanation

Chemical Analysis

Read Explanation

Kinetics

Read Explanation

Organic Chemistry

Read Explanation

Chemistry Branches

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.