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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. (鈥�2-ol鈥� 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

Question: Arrange each group of compounds in order of increasing basicity.

  1. CH3COO-,CICH2C00- , and PhO-
  2. sodium acetylide, sodium amide, and sodium acetate
  3. sodium benzoate, sodium ethoxide, and sodium phenoxide
  4. pyridine, sodium ethoxide, and sodium acetate

Question:

  1. Determine the structure of the carboxylic acid whose proton NMR spectrum appears below.
  2. Draw the NMR spectrum you would expect from the corresponding aldehyde whose oxidation gives this carboxylic acid.
  3. Point out two distinctive differences in the spectra of the aldehyde and the acid.

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline.

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Question: Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(a)propiophenone from propionic acid (two ways, using alkylation of the acid and using Friedel-Crafts acylation)

(b)methyl cyclohexyl ketone from cyclohexanecarboxylic acid
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