Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 30.SE, Problem 19AP
Interpretation Introduction
Interpretation:
The pericyclic reactions involved in the reaction shown are to be identified and how the rearrangement occurs also is to be indicated.
Concept introduction:
An electrocyclic reaction involves the cyclization of a conjugated acyclic system. These reactions are reversible and are highly stereospecific.
In elecrocyclic reactions involving even number of electron pairs, a thermal reaction occurs in conrotatory manner and a photochemical reaction occurs in disrotatory manner.
In elecrocyclic reactions involving odd number of electron pairs, a thermal reaction occurs in disrotatory manner and a photochemical reaction occurs in conrotatory manner.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Identify the following pericyclic reaction; explain the course and stereochemistry of the reaction.
The transformation takes place via two sequential pericyclic reactions. Identify the two reactions and give a critical explanation whether the reactions are allowable or not. Explain the stereochemistry.
The hydroboration–oxidation of internal alkynes produces ketones.(a) When hydroboration–oxidation is applied to but-2-yne, a single pure product isobtained. Determine the structure of this product, and show the intermediates in itsformation.
Chapter 30 Solutions
Organic Chemistry
Ch. 30.1 - Prob. 1PCh. 30.3 - Prob. 2PCh. 30.3 - Prob. 3PCh. 30.4 - Prob. 4PCh. 30.6 - What stereochemistry would you expect for the...Ch. 30.6 - Prob. 6PCh. 30.7 - Prob. 7PCh. 30.8 - Propose a mechanism to account for the fact that...Ch. 30.8 - When a 2, 6-disubstituted allyl phenyl ether is...Ch. 30.9 - Prob. 10P
Ch. 30.SE - Predict the product obtained when the following...Ch. 30.SE - Prob. 12VCCh. 30.SE - The following rearrangement of N-allyl-N,...Ch. 30.SE - Plastic photochromic sunglasses are based on the...Ch. 30.SE - Prob. 15MPCh. 30.SE - Prob. 16MPCh. 30.SE - Prob. 17MPCh. 30.SE - Prob. 18APCh. 30.SE - Prob. 19APCh. 30.SE - Prob. 20APCh. 30.SE - Prob. 21APCh. 30.SE - Prob. 22APCh. 30.SE - Prob. 23APCh. 30.SE - Prob. 24APCh. 30.SE - Prob. 25APCh. 30.SE - Prob. 26APCh. 30.SE - Prob. 27APCh. 30.SE - Prob. 28APCh. 30.SE - Propose a pericyclic mechanism to account for the...Ch. 30.SE - Prob. 30APCh. 30.SE - Prob. 31APCh. 30.SE - Prob. 32APCh. 30.SE - Prob. 33APCh. 30.SE - Bicyclohexadiene, also known as Dewar benzene, is...Ch. 30.SE - Prob. 35APCh. 30.SE - Prob. 36APCh. 30.SE - The 1H NMR spectrum of bullvalene at 100 C...Ch. 30.SE - Prob. 38APCh. 30.SE - Prob. 39APCh. 30.SE - Prob. 40APCh. 30.SE - In light of your answer to Problem 30-40, explain...
Knowledge Booster
Similar questions
- For each one of the following reactions, show step by step mechanism of the reactions and indicate the stereochemistry of the products and their relationshiparrow_forwardWhen 3-bromo-1-methylcyclohexene undergoes solvolysis in hot ethanol, two productsare formed. Propose a mechanism that accounts for both of these productsarrow_forwardSynthesis. Supply the reagents required to accomplis the following syntheses. Indicate the relative stereochemistry, where applicable, of the products obtained at each step.arrow_forward
- Identify the following pericyclic reaction; explain the course, product distribution and stereochemistry of the reaction. Where the first product is produced 70% and the second product is produced 30%.arrow_forwardIdentify the pericyclic reaction benzocyclobutane E undergoes on heating, give astructure for intermediate H, and provide a mechanism that accounts for itsformation.arrow_forwardClassify the following sigmatropic rearrangement and determine whether it takes place readily under thermal or photochemical reaction conditions.arrow_forward
- 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.arrow_forwardConsider the following chemical transformation:The transformation takes place via two sequential pericyclic reactions. Identify the two reactions and give a critical explanation whether the reactions are allowable or not. Explain the stereochemistryarrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you