Chapter 17: Q 32 E (page 567)
Question:The conversion of 3° alcohols into alkenes under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.
a)

b)

c)

Short Answer
a)

b)

c)

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Chapter 17: Q 32 E (page 567)
Question:The conversion of 3° alcohols into alkenes under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.
a)

b)

c)

a)

b)

c)

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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.

Question: Give IUPAC names for the following compounds:






p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have pKa 5 7.15, but 3,5-dimethyl-4-nitrophenol has pKa 5 8.25. Why is 3,5-dimethyl-4- nitrophenol so much less acidic?

What products would you obtain from reaction of 1-pentanol with thefollowing reagents?
(a)
(b)
(c)
(d) Dess- Martin periodinane
Compound A, , has the IR and NMR spectra shown. Proposea structure consistent with the observed spectra, and label each peak inthe NMR spectrum. Note that the absorption at disappears when is added.

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