When 2,2-dimethylcyclohexanol is treated with acid,1,2-dimethylcyclohexene and iso-propylidenecyclopentane are the products obtained. Draw a detailed mechanism thatexplains this result.CH 3CH3CH3H3O*CH3OHCH3CH31,2-dimethyl-isopropylidene-cyclopentane2,2-dimethyl-cyclohexanolcyclohexene

The details mechanism is given below.Explanation:

Answered: When 2,2-dimethylcyclohexanol is…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter22: Reactions Of Benzene And Its Derivatives

Section: Chapter Questions

Problem 22.23P

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When 2,2-dimethylcyclohexanol is treated with acid, 1,2-dimethylcyclohexene and iso- propylidenecyclopentane are the products obtained. Draw a detailed mechanism that explains this result. CH3 H3O+ CH3 CH3 CH3 OH CH3 CH3 2,2-dimethyl- cyclohexanol 1,2-dimethyl- isopropylidene- cyclopentane cyclohexene
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs via a nucleophilic substitution pathway. The reaction is 100% stereospecific.
The reaction of (S)-2-bromopentane with potassium cyanide to yield 2-methylpentanenitrile (2-cyanopentane) occurs due to a nucleophilic substitution pathway. The reaction is 100% stereospecific. Please explain what this observation tells about the mechanism of the reaction.
When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results? 1-ethoxypentane 1-methoxypentane 3-ethoxypentane 2-ethoxypentane 2-methoxypentane
(b) Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane (85%) and cyclohexyl acetate (15%). Propose a mechanism for the formation of the latter product using curly arrows. Br оссH, CH,COH + HBr 85% 15%
A step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.
Cyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.
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:
When cis-2-decalone is dissolved in ether containing a trace of HCl, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. Propose a mechanism for this isomerization and account for the fact that the trans isomer predominates at equilibrium.
When diethyl ether (CH3CH2OCH2CH3) is treated with concentrated HBr, the initial products are CH3CH2Br and CH3CH2OH. Propose a mechanism to account for this reaction.
Draw reaction mechanisms with all reactants, arrows, intermediates, and products. Your mechanism must account for all the products if more than one product is formed. 4-methycyclohexanol with phosphoric acid H3PO4 to for 1-methycyclohexene, 3- methylcyclohexene and 4-methycyclohexene
2) How would you synthesize the following compounds from cyclohexanone? CH₂Br A Br B CH₂C6H5 D CH2CH2CO2H

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