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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 to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

(b)

(c)

Tributylin hydride (Bu3SnH)is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. You job is to develop a mechanism, using the following reaction as an example.

The following bond-dissociation enthalpies may be helpful:

(a) Propose initiation and propagation steps to account for this reaction.

(b) Calculate values of ΔH for your proposed steps to show that they are energetically feasible. (Hint: A trace of Br2 and light suggests it’s there only as an initiator, to create Brradicals. Then decide which atom can be extracted most favorably from the starting materials by the Brradical. That should complete the initiation. Finally, decide what energetically favored propagation steps will accomplish the reaction).

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.

Glutathione (GSH) is a tripeptide that serves as a mild reducing agent to detoxify peroxides and maintain the cysteine residues of hemoglobin and other red blood cell proteins in the reduced state. Complete hydrolysis of glutathione gives Gly, Glu, and Cys. Treatment of glutathione with carboxypeptidase gives glycine as the first free amino acid released. Treatment of glutathione with 2,4-dinitrofluorobenzene (Sanger reagent, Problem 24-21, page 1282), followed by complete hydrolysis, gives the 2,4-dinitrophenyl derivative of glutamic acid. Treatment of glutathione with phenyl isothiocyanate does not give a recognizable phenylthiohydantoin, however.

(a) Propose a structure for glutathione consistent with this information. Why would glutathione fail to give a normal product from Edman degradation, even though it gives a normal product from the Sanger reagent followed by hydrolysis?

(b) Oxidation of glutathione forms glutathione disulfide(GSSG). Propose a structure for glutathione disulfide, and write a balanced equation for the reaction of glutathione with hydrogen peroxide.

Question: Show how you would synthesize the following carboxylic acids, using the indicated starting materials.

(a) hex-3-yne→propanoicacid

(b) cis-cyclodecene→decanedioicacid

(c ) iodobenzene→phenylaceticacid

(d)pentan-3-ol→2-ethylbutanoicacid

(e)o-xylene→phthalicacid

(f) allylbromide→but-3-enoicacid
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