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Chapter 17: Q 6 TP (page 857)

Do a retrosynthetic analysis on each of the following compounds, ending with the given starting materials:

(a)

(b)

Short Answer

Expert verified

Answer:

(a)

(b)

Step by step solution

01

Retrosynthesis

Retrosynthesis is defined as a logical approach for designing an organic synthesis that involves a breaking down of target molecules into available or given starting material by the imaginary breaking of bonds.

02

Ozonolysis

Ozonolysis refers to an organic chemical reaction where the unsaturated bonds of alkenes, alkynes, or azo compounds are cleaved with ozone O3.

Alkenes undergo oxidation with the help of ozone to give alcohols, aldehydes, ketones, and carboxylic acids.

Oxidation of alkynes with ozone gives acid anhydrides or diketones.

03

Retrosynthesis of reaction (a)

(a) The retrosynthetic analysis of reaction (a), ending with the given starting material is shown below in the figure:

04

Retrosynthesis of reaction (b)

(b) The retrosynthetic analysis of reaction (b), ending with the given starting material is shown below in the figure:

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Most popular questions from this chapter

How could you prepare the following compound using a starting material that contains no more than three carbons?

Draw the products of the following reactions:

a.

b.

Alkylation of the following compound with methyl iodide under two different conditions forms two different ketoesters (A and B). Each ketoester forms a cyclic diketone (C and D) when treated with methoxide ion in methanol.

a. Draw the structures of A and B, and indicate the conditions used in the alkylation reaction that cause that ketoester to be formed.

b. Draw the mechanism for the conversion of A to C.

In the presence of excess base and excess halogen, a methyl ketone is converted to a carboxylate ion. The reaction is known as the haloform reaction because one of the products is haloform (chloroform, bromoform, or iodoform). Before spectroscopy became a routine analytical tool, the haloform reaction served as a test for methyl ketones: the formation of iodoform, a bright yellow compound, signaled that a methyl ketone was present. Why do only methyl ketones form a haloform?

Draw the products of the following reactions:

a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl

b. pentanoic acid + PBr3 + Br2, followed by hydrolysis

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

d. diethyl 2-ethylhexanedioate: (1) sodium ethoxide; (2) HCl

e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + ∆

f. acetophenone + LDA/THF: (1) slow addition of diethyl carbonate; (2) HCl
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