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Concept explainers
Interpretation:
Given that when a
Concept introduction:
Under basic conditions the monohalogenated ketone further reacts to give dihalogenated products since the halo substituted ketone is much more reactive than the ketone.
To explain:
The difference in reactivity based on the observation given that when a ketone is treated with an acid and a halogen, the α-monohalogenated product can be obtained in high yield. However under basic conditions it is extremely difficult to isolate the monohalogenated product.
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Chapter 22 Solutions
Organic Chemistry
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardAcid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardsingle reaction sequence: a certain ketone undergoes alkylation to give new ketone, when reacted with a base and then an alkylating agent, 1-bromopropane. What is the structure of the final ketone product?arrow_forward
- A ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the alpha-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?arrow_forwardNon-conjugated β,γ-unsaturated ketones, such as 3-cyclohexenone, as in acid-catalysed equilibrium with their α,β-unsaturated isomers. The mechanism has several intermediates. Draw the structure of the second reaction intermediate in the conversion of 3-cyclohexenone to 2-cyclohexenone. This intermediate is a neutral compound.arrow_forwardA ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the α-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?arrow_forward
- When (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forwardIn the presence of an acid catalyst, acetaldehyde forms a trimer known as paraldehyde. Because it induces sleep when it is administered to animals inlarge doses, paraldehyde is used as a sedative or hypnotic. Propose a mechanism for the formation of paraldehyde.arrow_forwardThe ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.arrow_forward
- Tranexamic acid, a drug useful against blood clotting, is prepared commercially from p-methylbenzonitrile. Following is one of the steps in its synthesis, draw the structure of the product of this step.arrow_forwardUse the Witting reaction to answer the following question.arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Write the mechanism for each of the two reactions.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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