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Chapter 20: Q9P (page 1038)

Show how you would synthesize 2-phenylhex-3-yn-2-ol, starting with acetophenone (PhCOCH3 ) and any other reagents you need. (“2-ol” means there is an OH group on C2.)

Short Answer

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acetophenone 2-phenylhex-3-yn-2-ol

Step by step solution

01

Acetylide ions

Acetylide is an anion that can be prepared through the abstraction of acetylene proton from terminal alkyne, as it is a strong acid in comparison to other hydrocarbons.This is also known as the conjugate base of acetylene.

02

Synthesis of 2-phenyl3-yne-2-ol starting from acetophenone

Acetophenone is a ketone with one alkyl group and one phenyl group bonded to the carbonyl carbon. Tertiary alcohol can be formed by adding an acetylide, followed by protonation. The three groups bonded to the carbinol carbon atom are the acetylide, the alkyl and the phenyl groups of the acetophenone.

Hence, 2-phenylhex-3-yn-2-ol can be synthesized by adding acetylide (but-1-yn-1-ide) to acetophenone and hydronium ion.

acetophenone 2-phenylhex-3-yn-2-ol

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Most popular questions from this chapter

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

a)


b)



c)

Predict the productsand propose mechanisms for the following reactions.

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(a)trans-1-bromobut-2-ene→trans-pent-3-enoic acid (two ways)

(b)hex-3-ene→propanoic acid

(c) but-2-enal→but-2-enoic acid

(d) hexanoic acid→hexanal

(e)

(f)

(g)

(h)

Phenols (pKa≈ 10) are more acidic than other alcohols, so they are easily deprotonated by sodium hydroxide or potassium hydroxide. The anions of phenols (phenoxide ions) can be used in the Williamson ether synthesis, especially with very reactive alkylating reagents such as dimethyl sulfate. Using phenol, dimethyl sulfate, and other necessary reagents, show how you would synthesize methyl phenyl ether.
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