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Chapter 22: Q 69P-b (page 1204)

Question: Predict the products of the following reactions

b. 1phenylethanol + I2 excess

Short Answer

Expert verified

Answer

Step by step solution

01

Haloform reaction

The reaction occurs with the ketone in which halogenation occurs at the alpha carbon or the methyl carbon of ketone, and halogenation is occur three times from trihalomethane ketone, which is a best leaving group, then by proton transfer formation of acid occurs.

02

Reaction of 1phenylethanol + I2 excess

I2 is the oxidizing agent, and alcohol shows a positive test of iodoform, so iodine converts alcohol to ketone, which shows a haloform reaction to form tri halomethyl ketone followed by the proton transfer to form acid

03

Mechanism

Mechanism

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Most popular questions from this chapter

Predict the major products of the following reactions.

c)

Give the expected products for the aldol condensations of

  1. propanal.
  2. phenylacetaldehyde
  3. pentan-3-one.

A reaction involved in the metabolism of sugars is the splitting of fructose-1,6-diphosphate to give glyceraldehyde3-phosphate and dihydroxyacetone phosphate. In the living system, this retro-aldol is catalyzed by an enzyme called aldolase; however, it can also be catalyzed by a mild base. Propose a mechanism for the base-catalyzed reaction

The Knoevenagel condensation is a special case of the aldol condensation in which an active methylene compound reacts with an aldehyde or ketone, in the presence of a secondary amine as a basic catalyst, to produce a new C=C. Show the starting materials that made each of these by a Knoevenagel condensation.

In Solved Problem 22-9, the target molecule was synthesized using a Michael addition to form the bond that is β,γ to the upper carbonyl group. Another approach is to use a Michael addition to form the bond that isβ,γto the other (lower) carbonyl group. Show how you would accomplish this alternative synthesis.
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