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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Predict the products of the sulfuric acid-catalyzed dehydration of the following alcohols. When more than one product is expected, label the major and minor products.
(a) 2-methylbutan-2-ol (b) pentan-1-ol (c) pentan-2-ol
(d) 1-isopropylcyclohexanol (e) 2-methylcyclohexanol
Predict the major products (including stereochemistry) when trans-3-methylcyclohexanol reacts with thefollowingreagents.
(a) PBr3
(b) SOCl2
(c) Lucas reagent
(d) concentrated HBr
(e) TsCl/pyridine, then NaBr
When 1-cyclohexylethanol is treated with concentrated aqueous, the major product is 1-bromo-1-ethylcyclohexane.

(a)Propose a mechanism for this reaction.
(b) How would you convert 1-cyclohexylethanol to (1-bromoethyl)cyclohexane in good yield?

Show how you would use a simple chemical test to distinguish between the following pairs of compounds. Tell what you would observe with each compound.
(a)isopropyl alcohol andtert-butyl alcohol
(b)isopropyl alcohol and butan-2-one, CH3COCH2CH3
(c)hexan-1-ol and cyclohexanol
(d)allyl alcohol and propan-1-ol
(e)butan-2-one andtert-butyl alcohol
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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