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Chapter 9: Q40P (page 495)

Show how you would convert the following starting materials into the target compound. You may use any additional reagents you need.

Short Answer

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Multistep synthesis forms an important part of organic reactions. It is a reaction where the starting material is transformed into a final product through several reactions.

Step by step solution

01

Multistep synthesis

Multistep synthesis forms an important part of organic reactions. It is a reaction where the starting material is transformed into a final product through several reactions.

02

Reaction of alkynes

Alkynes undergo several reactions, and one among those is the deprotonation. The deprotonation of alkynes gives rise to alkynes when sodium amide is used as a reagent.

03

Conversion of the following starting materials into the target compound

Benzyl bromide reacts with acetylene in the presence of sodium amide to form an anion. The reaction can be given as:

The generated anion reacts with the carbonyl group of the aldehyde, followed by acid-catalyzed dehydration in the presence of sulphuric acid and heat. This is followed by the incorporation of meta-chloroperoxybenzoic acid (mCPBA) to create the target molecule. The reaction can be given as:

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Most popular questions from this chapter

For each compound, give the product(s) expected from (1) HgSO4/H2SO4– catalyzed hydration and (2) hydroboration–oxidation.

(a) hex-1-yne

(b) hex-2-yne

(c) hex-3-yne

(d) cyclodecyne

When pent-2-yne reacts with mercuric sulfate in dilute sulfuric acid, the product is a mixture of two ketones. Give the structures of these products, and use mechanisms to show how they are formed.

Question: Predict the products of the following acid-base reactions, or indicate if no significant reaction would take place.

(a)H-C≡C-H+NaNH2(b)H-C≡C-H+CH3Li(c)H-C≡C-H+NaOCH3(d)H-C≡C-H+NaOH(e)H-C≡CNa++NaOH(f)H-C≡CNa++H2O(g)H-C≡CNa++H2C=CH2(h)H2C=CH2+NaNH2(i)CH3OH+NaNH2

The hydroboration–oxidation of internal alkynes produces ketones.

(a) When hydroboration–oxidation is applied to but-2-yne, a single pure product is obtained. Determine the structure of this product, and show the intermediates in its formation.

(b) When hydroboration–oxidation is applied to pent-2-yne, two products are obtained. Show why a mixture of products should be expected with any unsymmetrical internal alkyne.

Show how you would convert

(a) oct-3-yne to cis-oct-3-ene.

(b) pent-2-yne to trans-pent-2-ene.

(c) cis-cyclodecene to trans-cyclodecene.

(d) but-1-yne to cis-hex-3-ene.
See all solutions

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