Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 30.SE, Problem 29AP
Propose a pericyclic mechanism to account for the following transformation:
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Treatment of trans-2-chlorocyclohexanol with NaOH yields 1, 2-epoxy-cyclohexane, but reaction of the cis isomer under the same conditions yields cyclohexanone. Propose mechanisms for both reactions, and explain why the different results are obtained.
In a strongly acidic solution, cyclohexa-1,4-diene tautomerizes to cyclohexa-1,3-diene.Propose a mechanism for this rearrangement, and explain why it is energetically favorable
Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane
(85%) and cyclohexyl acetate (15%).
Br
OCCH
CH,COH
+ HBr
Bromocyclohexane Cyclohexyl acetate
(15%)
Cyclohexene
(85%)
Propose a mechanism for the formation of the latter product.
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...
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- Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardIdentify the following pericyclic reaction; explain the course and stereochemistry of the reaction.arrow_forward
- Show how the following starting material is converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.arrow_forwardShow how the following starting materials are converted to the given product by a series of two pericyclic reactions. Account for the observed stereochemistry.arrow_forwardTreatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products (M and N) with molecular formula C6H12. The 1H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation.arrow_forward
- Propose a reaction mechanism for the following transformation:arrow_forwardWhat reagents are needed to carry out the following syntheses?arrow_forwardWhen cyclohexene is treated with bromine in saturated aqueous sodium chloride, a mixture of trans-2-bromocyclohexanol and trans-1-bromo-2-chlorocyclohexane results.Propose a mechanism to account for these two products.arrow_forward
- Synthesize the following compound from benzonitrile (C6H5CN):arrow_forwardPropose a mechanism and predict the product, including stereochemistry.arrow_forwardTreatment of W with CH3Li, followed by CH3I, affords compound Y (C7H14O) as the major product. Y shows a strong absorption in its IR spectrum at 1713 cm−1, and its 1H NMR spectrum is given below. (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y.arrow_forward
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