Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 12: Q.65. (page 493)

Question:Devise a synthesis of (E)-hex-2-ene from pent-1-ene and any needed organic compounds or inorganic reagents.

Short Answer

Expert verified

Answer

Step by step solution

01

Conversion of 1-pentene to 1-pentyne

An alkene can be converted to an alkyne via a geminal dihalide intermediate. A strong base like can be used for the conversion of dihalide to the desired alkyne.The reaction is shown below:

Conversion of 1-pentene to 1-pentyne

02

Conversion of 1-pentyne to 1-hexyne

The 1-pentyne formed in a previous step is treated with a strong base for its corresponding acetylide anion to form, which is further treated with bromomethane to form 2-hexyne.The reaction is shown below:

Conversion of 1-pentyne to 1-hexyne

03

Formation of (2E)-2-hexene from 2-hexyne

The anti-addition of hydrogen to 2-hexyne can be performed using the reagent sodium in liquid ammonia. The reaction is known as Birch reduction.The reaction is given below:

Formation of (2E)-2-hexene

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

Question: Epoxidation of the following allylic alcohol using the Sharpess reagent (-)-DET gives two epoxy alcohols in a ratio of 87:13.

  1. Assign structures to the major and minor product.
  2. What is the enantiomeric excess in this reaction?

Question: What product is formed when CH3OCH2CH2C≡CCH2CHCH32 is treated with each reagent: (a) H2 (excess), Pd-C; ; (b) H2(1 equiv), Lindlar catalyst; (c) H2(excess), Lindlar catalyst; (d) Na,NH3 ?

Question: The Birch reduction is a dissolving metal reaction that converts substituted benzenes to cyclohexa-1,4-dienes using Li and liquid ammonia in the presence of an alcohol. Draw a stepwise mechanism for the following Birch reduction.

Question:What epoxide is formed when each alkene is treated with mCPBA?

a.

b.


c.

Question: a) What product is formed in Step [1] of the following reaction sequence?

(b) Draw a mechanism for Step [2] that accounts for the observed stereochemistry.

(c) What reaction conditions are necessary to form chiral A from prop-2-en-1-ol

See all solutions

Recommended explanations on Chemistry Textbooks

Organic Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

Read Explanation

Nuclear 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