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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

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (鈥�3-ol鈥� means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

(c)

(d) meso-hexane-3,4-diol

(a)Count the elements of unsaturation in cicutoxin, capillin, and panaxytriol.

(b) Draw structural formulas of at least two alkynes of each molecular formula.

(1) C5H8 (2) C8H10 (3) C9H12

Question: Predict the products formed when CH3CH2-C鈮�C:Na+ reacts with the following compounds.

(a)ethyl bromide

(b)tert-butyl bromide

(c)formaldehyde

(d)cyclohexanone

(e)CH3CH2CH2CHO

(f)cyclohexanol

(g)butan-2-one,CH3CH2COCH3

Predict the product(s) you would expect from the treatment of each compound with (1) dilute, neutral and (2) warm basic , then dilute acid.

(a) hex-1-yne (b) hex-2-yne (c) hex-3-yne

(d) 2-methylhex-3-yne (e) cyclodecyne

Question:Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)

(a)cis-cyclooctene

(b)cyclooctane

(c)trans-1,2-dibromocyclooctane

(d)cyclooctanone

(e)1,1-dibromocyclooctane

(f)3-bromocyclooctene

(g)cyclooctane-1,2-dione

(h)

(i)
See all solutions

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