EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 17, Problem 17.51AP
Interpretation Introduction

(a)

Interpretation:

A curved-arrow mechanism for the cyclization of 2,3- oxidosqualene is to be stated.

Concept introduction:

A chemical reaction in organic chemistry which is used for the synthesis of cyclopentenones is known as cyclization reaction.

The nucleophilic substitution reactions are the reactions in which one nucleophile attacks the electrophilic center and eliminates another group in the compound. These reactions depend upon the nucleophilicity and concentration of the nucleophile.

The SN2 reaction is a nucleophilic substitution bimolecular single-step reaction in which the addition of nucleophile and removal of the leaving group takes place simultaneously.

Interpretation Introduction

(b)

Interpretation:

A curved-arrow mechanism for the cyclization of 2,3- oxidosqualene is to be stated.

Concept introduction:

A chemical reaction in organic chemistry which is used for the synthesis of cyclopentenones is known as cyclization reaction.

The nucleophilic substitution reactions are the reactions in which one nucleophile attacks the electrophilic centre and eliminates another group in the compound. These reactions depend upon the nucleophilicity and concentration of the nucleophile.

The SN2 reaction is a nucleophilic substitution bimolecular single step reaction in which the addition of nucleophile and removal of leaving group takes place simultaneously

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The natural product halomon could theoretically arise from another naturally occurring compound known as myrcene. To accomplish this, a biochemical process that could deliver the synthetic equivalent of BrCi to all three double bonds would be required. (Chem Comm. 2014, 50, 13725) (a) Using three molar equivalents of BrCL please provide a mechanism to account for the formation of the bracketed structure (you do not need to show stereochemistry in this mechanism) HB (3 equiv) myrcene balomon 8.61a Add curved arrow(s) to show the mechanism steps. Edit Drawing sits
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(a) Recall, from WP 14.26 (and from lecture), cyclopentadienone and cycloheptatrienone differ drastically in reactivity and stability. One is very stable and unreactive, and the other one is very reactive and rapidly undergoes a dimerization reaction. Which one is particularly stable? Explain why. For the one which is extremely reactive, explain why, but also draw the structure of the dimer which is formed rapidly.
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