Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 26, Problem 26.49P

Draw the product formed from the ring-closing metathesis of each compound. Then, devise a synthesis of each metathesis starting material from benzene, alcohols with less than five carbons, and any needed organic and inorganic reagents.

a. Chapter 26, Problem 26.49P, 26.49 Draw the product formed from the ring-closing metathesis of each compound. Then, devise a , example  1 b. Chapter 26, Problem 26.49P, 26.49 Draw the product formed from the ring-closing metathesis of each compound. Then, devise a , example  2

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The product formed from the ring-closing metathesis of given compound is to be drawn, and the synthesis of metathesis starting material using CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganic reagents is to be stated.

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 to Problem 26.49P

The product formed from the ring-closing metathesis of given compound is

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  1

The synthesis of metathesis starting material using CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganic reagents is,

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  2

Explanation of Solution

The given compound is a diene.

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.

The product formed from the ring-closing metathesis of given compound is drawn in Figure 1.

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  3

Figure 1

The synthesis of metathesis starting material involves ten steps. The first step is Friedel-Crafts alkylation of benzene with 1,1-dichloropropane in the presence of AlCl3 catalyst to yield the (1-chloropropyl) benzene. The second step is treatment of (1-chloropropyl) benzene with water to yield 1-phenylpropan-1-ol. The third step is protection of the OH group by TMSCl. The fourth step is chlorination of protected alcohol in the presence of hv. The fifth step is nucleophilic attack of OH on the carbon atom of CCl bond to convert it into corresponding alcohol (1ο). The sixth step is oxidation of primary alcohol by PCC to convert it into corresponding aldehyde. The seventh step is Wittig reaction with CH2=PPh3 to convert the C=O bond of CHO group to the C=C bond. The eighth step is deprotection of the OH group (protected by OTMS) group by TBAF. The ninth step is conversion of the OH group to the alkoxide salt by NaH. The tenth step is treatment of alkoxide salt with 3-chloroprop-1-ene to yield the desired product.

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  4

Figure 2

Conclusion

The product formed from the ring-closing metathesis of given compound is drawn in Figure 1. The synthesis of metathesis starting material using CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganic reagents is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The product formed from the ring-closing metathesis of given compound is to be drawn, and the synthesis of metathesis starting material using CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganic reagents is to be stated.

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 to Problem 26.49P

The product formed from the ring-closing metathesis of given compound is,

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  5

The synthesis of metathesis starting material using CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganic reagents is,

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  6

Explanation of Solution

The given compound is a diene.

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.

The product formed from the ring-closing metathesis of given compound is drawn in Figure 3.

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  7

Figure 3

The synthesis of metathesis starting material involves nine steps. The first step is Friedel-Crafts alkylation of benzene with chloromethane in the presence of AlCl3 catalyst to yield toluene. The second step is oxidation of toluene by CrO2Cl2 (chromyl chloride) to yield benzaldehyde. The third step is Wittig reaction of benzaldehyde with CH2=PPh3 to yield styrene. The fourth step is hydroboration oxidation of styrene to yield 2-phenylethanol (1οalcohol). The fifth step is oxidation of primary alcohol by PCC to convert it into corresponding aldehyde (3-phenylpropanal). The sixth step is Wittig reaction of 3-phenylpropanal with CH2=PPh3 to yield allylbenzene. The seventh step is hydroboration oxidation of allylbenzene to yield 3-phenylpropan-1-ol (1οalcohol). The eighth step is oxidation of primary alcohol by PCC to convert it into corresponding aldehyde. The ninth step is acetal formation, using two equivalents of prop-2-en-1-olin the presence of TsOH to yield the desired compound.

Organic Chemistry, Chapter 26, Problem 26.49P , additional homework tip  8

Figure 4

Conclusion

The product formed from the ring-closing metathesis of given compound is drawn in Figure 3. The synthesis of metathesis starting material using CH2(CO2Et)2, alcohols with less than five carbons, and any needed organic and inorganic reagents is shown in Figure 4.

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Chapter 26 Solutions

Organic Chemistry

Ch. 26 - Problem 26.11 What product is formed when each...Ch. 26 - Prob. 26.12PCh. 26 - Problem 26.13 Draw the products formed when each...Ch. 26 - Problem 26.14 What products are formed when ...Ch. 26 - Problem 26.15 Draw the product formed from...Ch. 26 - What product is formed by ring-closing metathesis...Ch. 26 - Problem 26.17 What starting material is needed to...Ch. 26 - 26.18 In addition to organic halides, alkyl...Ch. 26 - 26.19 What product is formed by ring-closing...Ch. 26 - 26.20 Draw the products formed in each...Ch. 26 - What organic halide is needed to convert lithium...Ch. 26 - 26.22 How can you convert ethynylcyclohexane to...Ch. 26 - 26.23 What compound is needed to convert styrene...Ch. 26 - 26.24 What steps are needed to convert to octane...Ch. 26 - Prob. 26.25PCh. 26 - Prob. 26.26PCh. 26 - 26.27 Draw the products (including stereoisomers)...Ch. 26 - 26.28 Treatment of cyclohexene with and forms...Ch. 26 - Prob. 26.29PCh. 26 - 26.30 What starting material is needed to prepare...Ch. 26 - Prob. 26.31PCh. 26 - Prob. 26.32PCh. 26 - When certain cycloalkenes are used in metathesis...Ch. 26 - 26.34 Draw the products formed in each reaction. ...Ch. 26 - Prob. 26.35PCh. 26 - Draw a stepwise mechanism for the following...Ch. 26 - Sulfur ylides, like the phosphorus ylides of...Ch. 26 - Although diazomethane is often not a useful...Ch. 26 - Prob. 26.39PCh. 26 - Prob. 26.40PCh. 26 - Prob. 26.41PCh. 26 - Prob. 26.42PCh. 26 - 26.43 Devise a synthesis of each compound using a...Ch. 26 - 26.44 Devise a synthesis of each compound from...Ch. 26 - 26.45 Devise a synthesis of each compound from...Ch. 26 - 26.46 Devise a synthesis of each substituted...Ch. 26 - Biaryls, compounds containing two aromatic rings...Ch. 26 - Prob. 26.48PCh. 26 - 26.49 Draw the product formed from the...Ch. 26 - Prob. 26.50PCh. 26 - 26.51 Devise a synthesis of each of the following...Ch. 26 - Prob. 26.52PCh. 26 - 26.53 The following conversion, carried out in the...Ch. 26 - Prob. 26.54PCh. 26 - 26.55 Dimethyl cyclopropanes can be prepared by...Ch. 26 - Prob. 26.56P
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