(a)
Interpretation:
The reagent must be provided to achieve the given transformation.
Concept Introduction :
The OTs group is a good leaving group which can be displaced by simple nucleophilic substitution.
(b)
Interpretation:
The reagent must be provided to achieve the given transformation of alcohol to cyano compound.
Concept Introduction :
The OH group is a bad leaving group which can be displaced by cyanide after converting the OH to a good leaving group.
(c)
Interpretation:
The reagents must be provided for the conversion of tertiary alcohol to tertiary bromide.
Concept Introduction :
The tertiary alcohols can undergo acid catalyzed SN1 substitution.
(d)
Interpretation:
A suitable reagent must be provided for the conversion of chloro to thiol with inversion of configuration.
Concept Introduction :
The less hindered
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ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG(LL)
- When cis-2-decalone is dissolved in ether containing a trace of HCI, an equilibrium is established with trans-2-decalone. The latter ketone predominates in the equilibrium mixture. H H HCI cis-2-Decalone trans-2-Decalone Propose a mechanism for this isomerization and account for the fact that the trans iso- mer predominates at equilibrium.arrow_forward2) How would you synthesize the following compounds from cyclohexanone?: a) b) CO₂Harrow_forwardUsing your reaction roadmap as a guide, show how to convert cyclohexanol into racemic trans-1,2-cydohexanediol. Show all required reagents and all molecules synthesized along the way.arrow_forward
- Using your reaction roadmap as a guide, show how to convert butane into butanal. Show all reagents needed and all molecules synthesized along the way.arrow_forwardPropose an efficient synthesis (with mechanisms) for each of the following transformations: b) O O OH O CO₂Harrow_forwardWhich of the following compounds will not undergo keto-enol tautomerism? ОН OH ОН OH ОНarrow_forward
- Propose an efficient synthesis for each of the following transformations: Br NO2arrow_forwardAldehydes 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_forwardCyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning