ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
12th Edition
ISBN: 9781119304241
Author: Solomons
Publisher: WILEY C
bartleby

Concept explainers

Question
Book Icon
Chapter 13, Problem 11PP
Interpretation Introduction

Interpretation:

The transition states of exo and endo Diels Ander reactions of maleic anhydride with cyclopentadiene are to be drawn. Also, the transition state that leads to only one enantiomer need to be shown in each.

Concept introduction:

A Diels Ander reaction is one between a conjugate diene and a reactant containing a double bond (dienophile) to form a product. The product is called adduct.

Diels Ander reactions are highly stereospecific. The configuration of the dienophile is retained in the product and the reaction is a syn addition reaction.

The dienes react with dienophiles in cis forms rather than trans forms.

Endo and exo refer to the orientation of the dienophile and its electron-withdrawing group when it reacts with a diene in a Diels Ander reaction.

Endo is favored in the transition state of a Diels Ander reaction because it has a lower energy.

Blurred answer
Students have asked these similar questions
A solution of 5-methylcyclopenta-1,3-diene rearranges at roomtemperature to a mixture containing 1-methyl-, 2-methyl-, and 5-methylcyclopenta-1,3-diene. (a) Show how both isomeric products areformed from the starting material by a sigmatropic rearrangementinvolving a C–H bond. (b) Explain why 2-methylcyclopenta-1,3-diene isnot formed directly from 5-methylcyclopenta-1,3-diene by a [1,3]rearrangement.
4.35 Formulate the reaction of cyclohexene with (i) Br2 and (ii) meta-chloro- peroxybenzoic acid followed by H30+. Show the reaction intermediates and the final products with correct cis or trans stereochemistry. 4.36 What products would you expect to obtain from reaction of cyclohexa- 1,3-diene with each of the following? (a) 1 mol Br2 in CH2C12 (c) 1 mol DCl (D = deuterium, ²H) (b) 1 mol HCl (d) 2 mol H2 over a Pd catalyst 4.37 Predict the products of the following reactions on hex-1-yne: (a) 1 equiv HBr ? (b) 1 equiv Cl2 ? (c) H2, Lindlar catalyst
Many variations of ring-closing metathesis have now been reported. Tandem ring-opening-ring-closing metathesis can occur with cyclic alkenes that contain two additional carbon-carbon double bonds. In this reaction, the cycloalkene is cleaved, and two new rings are formed. [1] What compounds are formed in this tandem reaction with the following substrates? [2] Devise a synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethyl maleate as the dienophile.

Chapter 13 Solutions

ORGANIC CHEM. VOL.1+2-W/WILEYPLUS

Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning