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Chapter 12: Q.67. (page 493)

Question:Devise a synthesis of 1-phenyl-5-methylhexane [C6H5CH24CHCH32]from acetylene, alkylhalides, and any required inorganic reagents.

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01

Reaction of acetylene with isopropyl bromide

Acetylene is treated with a strong base to form an acetylide anion, which can further react with an alkyl halide to form a new alkyne.Using this mechanism, acetylene is treated with sodium hydride and then reacted with isopropyl bromide.

The reaction is shown below:

Formation of 1-phenyl-5-methyl-hex-3-yne

02

Reduction of 1-phenyl-5-methyl-hex-3-yne

The alkyne formed in the previous step is reduced to 1-phenyl-5-methylhexane upon treatment with hydrogen in the presence of a palladium catalyst.The reaction is shown below:

Formation of 1-phenyl-5-methylhexane

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Most popular questions from this chapter

Question: Explain why heats of hydrogenation cannot be used to determine the relative stability of 2-methylpent-2-ene and 3-methylpent-1-ene.

Question: Draw a stepwise mechanism for the reduction of epoxide A to alcohol B using LiAlH4 . What product would be formed if LiAlD4were used as reagent? Indicate the stereochemistry of all stereogenic centers in the product using wedges and dashed wedges.

Question: Draw the organic products formed when each alkene is treated with H2 / Pd-C. Indicate the three-dimensional structure of all stereoisomers formed.

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b.

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Question: Draw the organic products in each of the following reactions.

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