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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

Question:Predict the products of the reaction of but-1-yne with the following reagents.

(a)1 equivalent of HCl

(b)2 equivalents of HCl

(c)excess H2 , Ni

(d) H2 , Pd /BaSO4, quinolone

(e)1 equivalent of Br2

(f)2 equivalents of Br2

(g)cold, dilute KMnO4

(h)warm, concd.KMnO4 , NaOH

(i)Na, liquid ammonia

(j) NaNH2

(k) H2SO4/HgSO4, H2O

(l) Sia2BH, then , H2O2,OH-

For each molecular formula, draw all the isomeric alkynes, and give their IUPAC names. Circle the acetylenic hydrogen of each terminal alkyne.

(a) C5H8 (three isomers)

(b) C6H10 (seven isomers)

Disiamylborane adds only once to alkynes by virtue of its two bulky secondary isoamyl groups. Disiamylborane is prepared by the reaction of BH3. THF with an alkene.

(a) Draw the structural formulas of the reagents and the products in the preparation of disiamylborane.

(b) Explain why the reaction in part (a) goes only as far as the dialkylborane. Why is Sia3B not formed?

Propose a mechanism for the reaction of pent-1-yne with HBr in the presence of peroxides. Show why anti-Markovnikov orientation results.
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