Chapter 17: Q2P (page 528)
Draw structures corresponding to the following IUPAC names:
- (Z)-2-Ethyl-2-buten-1-ol
- 3-Cyclohexen-1-ol
- trans-3-Chlorocycloheptanol
- 1,4-Pentanediol
- 2,6-Dimethylphenol
- o-(2-Hydroxyethyl)phenol
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Chapter 17: Q2P (page 528)
Draw structures corresponding to the following IUPAC names:
Answer


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Dehydration of trans-2-methylcyclopentanol with POCl3 in pyridine yields predominantly 3-methylcyclopentene. Is the stereochemistry of this dehydration syn or anti? Can you suggest a reason for formation of the observed product? (Make molecular models!)
Reduction of 2-butanone with NaBH4yields 2-butanol. Is the product chiral? Is it optically active? Explain.
p-Nitrobenzyl alcohol is more acidic than benzyl alcohol, but p-methoxy-benzyl alcohol is less acidic. Explain.
For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.
(a)

(b)

(c)

Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to account for this reaction.

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