(a) Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted. Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Question

Want to see the full answer?

Answer 1

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resultingconjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.

Give the structure of the main product of each of the following Diels-Alder reactions. Make sureto show the stereochemistry of the products when unambiguous.

The endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rainforests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.

Answer 2

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Answer 6

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Answer 7

Chapter 26, Problem 26.50P

Interpretation Introduction

(a)

Interpretation: The compounds are formed by the tandem reaction with given substrates are to be predicted.

Concept introduction: The ring-closing metathesis (RCM) by Grubbs catalyst occurs, when the starting material is diene. This reaction is facilitated under high-dilution condition as it favors intramolecular metathesis instead of intermolecular metathesis.

Answer 8

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Answer 9

Interpretation Introduction

(b)

Interpretation: The synthesis of the substrate in part (b) that uses a Diels–Alder reaction with diethylmaleate as the dienophile is to be devised.

Concept introduction: Diels-alder reaction is a cycloaddition reaction in which two molecules combine to form a new ring. In this type of reaction, syn addition takes place. It is a reaction between diene with a dienophile to yield a cyclohexene. The dienophile adds to one side of the diene, and diene adds to the one side of the dienophile. Thus, they have syn stereochemistry.

Answer 10

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 13

Ch. 26 - Prob. 26.1P Ch. 26 - Prob. 26.2P Ch. 26 - Synthesize each product from the given starting...Ch. 26 - Prob. 26.4P Ch. 26 - Prob. 26.5P Ch. 26 - Prob. 26.6P Ch. 26 - Prob. 26.7P Ch. 26 - Problem 26.8 What starting materials are needed to...Ch. 26 - Prob. 26.9P Ch. 26 - Prob. 26.10P

Solution Summary: The author explains the ring-closing metathesis (RCM) by Grubbs catalyst occurs when the starting material is diene.

Concept explainers

Want to see the full answer?

Chapter 26 Solutions