Chapter 17: Q30E (page 567)
The conversion of 3° alcohols into 3° alkyl halides under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.

Short Answer

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Chapter 17: Q30E (page 567)
The conversion of 3° alcohols into 3° alkyl halides under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.


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Named bombykol, the sex pheromone secreted by the female silkworm
moth has the formula C16H28O and the systematic name (10E,12Z)-
10,12-hexadecadien-1-ol. Draw bombykol, showing the correct geometry
for the two double bonds.
Question: Give IUPAC names for the following compounds:






Draw the structure of the carbonyl compound(s) from which each of the following alcohols might have been prepared, and show the products you would obtain by treatment of each alcohol with (1) Na metal, (2) , and (3) Dess-Martin periodinane.
(a)

(b)

2,3-Dimethyl-2,3-butanediol has the common name pinacol. On heating with aqueous acid, pinacol rearranges to pinacolone, 3,3-dimethyl-2-butanone. Suggest a mechanism for this reaction.

Propose a synthesis of bicyclohexylidene, starting from cyclohexanone as the only source of carbon.

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