Concept explainers
Interpretation:
The correct enantiomer of
Concept introduction:
The alcohols on reaction with
As the hydroxyl group of alcohol acts as a nucleophile, there is no change in configuration of alcohol and tosylate (
The thiol can be prepared from
The
Want to see the full answer?
Check out a sample textbook solutionChapter 16 Solutions
Organic Chemistry - Standalone book
- When a primary alcohol is treated with p-toluenesulfonyl chloride at room temperature in the presence of an organic base such as pyridine, a tosylate is formed. When the same reaction is carried out at higher temperature, an alkyl chloride is often formed. Explain.arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. Show all required reagents and all molecules synthesized along the way.arrow_forward
- Reaction of N,N-diethyl-p-diaminobenzene with sodium nitrite and hydrochloric acid at 0°C, followed by treatment with nitrobenzene.arrow_forward(a) Draw the structures of the following compounds :(i) 4-Chloropentan-2-one (ii) p-Nitropropiophenone(b) Give tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(iii) Benzaldehyde and Acetophenonearrow_forwardThe reaction of a ketone and excess methanol with an acid as a catalyst gives what product? A) Hemiacetal B) Di-ether C) Hemiketal D) Acetal E) Ketalarrow_forward
- A racemic mixture of 2-methyl-1-phenyl-1-butanone is formed when (R)-2-methyl-1-phenyl-1-butanone is dissolved in an acidic or basic aqueoussolution. Give an example of another ketone that undergoes acid- or base-catalyzed racemization.arrow_forwardTo obtain 2,4,4-trimethyl-2-pentanal, write down the reaction mechanism using 2,2-dimethylpropanal and other necessary reagents.arrow_forwardTreatment of p-hydroxybenzoic acid with aqueous bromine leads to the evolution of carbon dioxide and the formation of 2,4,6-tribromophenol. Explain.arrow_forward
- How do you convert the following: (i) ethyl chloride is treated with Nal in the presence of acetone, (ii) chlorobenzene is treated with Na metal in the presence of dry ether, (iii) methyl chloride is treated with KNO2? Write chemical equations in support of your answer.arrow_forwardProvide the reagents necessary to convert (R)-2-chlorobutane to (S)-2-methoxybutane.arrow_forwardDraw a structural formula for the product formed by treating butanal with reagent. Q.) LiAlH4 followed by H2Oarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning