Chapter 11: Q30P (page 572)
Predict the products formed by periodic acid cleavage of the following diols
(a) 
(b) 
(c) 
(d) 
Short Answer
(a) 
(b)
(c)
(d) 
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Chapter 11: Q30P (page 572)
Predict the products formed by periodic acid cleavage of the following diols
(a) 
(b) 
(c) 
(d) 
(a) 
(b)
(c)
(d) 
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When cis-2-methylcyclohexanol reacts with the Lucas reagent, the major product is 1-chloro-1-methylcyclohexane. Propose a mechanism to explain the formation of this product.
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.

Show how you would synthesize the following compounds. As starting materials, you may use any alcohols containing four or fewer carbon atoms, cyclohexanol, and any necessary solvents and inorganic reagents.


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
Give the structures of the products you would expect when each alcohol reacts with
(1) HCl, ZnCl2; (2) HBr; (3) PBr3; (4) P/I2; and (5) SOCl2.
(a) butan-1-ol (b) 2-methylbutan-2-ol
(c) 2,2-dimethylbutan-1-ol (d) cis-3-methylcyclopentanol
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