Chapter 11: Q11P (page 554)
Predict the products of the following reactions.
(a) cyclohexylmethanol + TsCl / pyridine (b) product of (a) + LiAlH4
(c) 1- methylcyclohexanol + H2SO4, heat (d) product of (c) + H2, Pt
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Chapter 11: Q11P (page 554)
Predict the products of the following reactions.
(a) cyclohexylmethanol + TsCl / pyridine (b) product of (a) + LiAlH4
(c) 1- methylcyclohexanol + H2SO4, heat (d) product of (c) + H2, Pt




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Propose a mechanism for each reaction.
(a) 
(b) 
The Williamson ether synthesis involves the displacement of an alkyl halide or tosylate by an alkoxide ion. Would the synthesis shown be possible by making a tosylate and displacing it? If so, show the sequence of reactions. If not, explain why not and show an alternative synthesis that would be more likely to work.

Under acid catalysis, tetrahydrofurfuryl alcohol reacts to give surprisingly good yields of dihydropyran. Propose a mechanism to explain this useful synthesis.

(a)
(b)
(c)
(d) 
The compound shown below has three different types of OH groups, all with different acidities. Show the structure produced after this compound is treated with different amounts of NaH followed by a methylating reagent. Add a brief explanation.

(a)1 equivalent of NaH, followed by 1 equivalent of CH3l and heat
(b)2 equivalents of NaH, followed by 2 equivalents of CH3l and heat
(c) 3 equivalents of NaH, followed by 3 equivalents of CH3l and heat
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