Concept explainers
Interpretation:
The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride are to be shown.
Concept introduction:
The nucleophilic attack of the deuderide ion on the
To give:
The structure and stereochemistry of the alcohol that would result if 1, 2-epoxycyclohexane was reduced with Lithium aluminium deuteride.
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Chapter 18 Solutions
Organic Chemistry
- The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.arrow_forwardproduct would be formed if the four-membered ring alcohol in Problem 70 were heated with an equivalent amount of HBr rather than with acatalytic amount of H2SO4?arrow_forwardWhat factor seems to be responsible for the Wagner-Meerwein rearrangement of camphene to give isobornyl acetate (a 3º → 2º carbocation rearrangement)?arrow_forward
- (a) Arrange the following compounds in an increasing order of their indicated property :(i) Benzoic acid, 4-Nitrobenzoic acid, 3,4-Dinitrobenzoic acid, 4-Methoxybenzoic acid (acid strength)(ii) CH3CH2CH (Br) COOH, CH3CH (Br) CH2COOH,(CH3)2CHCOOH, CH3CH2CH2COOH (acid strength)(b) How would you bring about the following conversions :(i) Propanone to Propene (ii) Benzoic acid to Benzaldehyde(iii) Bromobenzene to 1-phenylethanolarrow_forward1. Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic hydrogenation over palladium catalyst to give B, C9H18. On the treatment with acidic KMnO4, compound A gives among other things, a ketone that was identified as cyclohexanone. On reaction with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A , B and C?arrow_forwardShow how to convert trans-4-methylcyclohexanol to cis-1-iodo-4methylcyclohexane via a tosylate.arrow_forward
- Hydride reduction (with LiAlH4 or NaBH4) of each of the following ketones has been reported in the chemical literature and gives a mixture of two diastereomeric alcohols in each case. Give the structures of both alcohol products for each ketone.(a) (S)-3-Phenyl-2-butanone(b) 4-tert-Butylcyclohexanonearrow_forwardIn the acid catalyzed dehydration of 2,2-dimethyl-1-cyclohexanol, draw all possible alkenes, including those resulting from rearrangement.arrow_forwardShow how the following compounds will be synthesized, beginning with benzene or toluene and any reagents required. Assume para, in ortho, para mixtures, are the main ingredients (and separable from ortho). 1) p-bromobenzene sulfonic acid 2) 1-phenypentane 3) m-chloronitrobenzene 4) o-chlorobenzoic acidarrow_forward
- When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be C5H10O. Propose a likely structure for this product, suggesting a reasonable mechanistic pathway for its formationarrow_forwardStarting with cis-3-hexene, show how to prepare the Racemic 3,4-hexanediol diolarrow_forwardElimination of HBr from 2-bromonorbornane gives only 2-norbornene and no 1-norbornene. How do you account for the regioselectivity of this dehydrohalogenation? In answering this question, you will find it helpful to look at molecular models of both 1-norbornene and 2-norbornene and analyze the strain in each.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning