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
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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Get started for freePropose a mechanism for each reaction.
(a)
(b)
Predict the products you expect when the following starting material undergoes oxidation with an excess of each of the reagents shown below.
(a)chromic acid
(b)PCC(pyridinium chlorochromate)
(c)sodium hypochlorite/ acetic acid
(d)DMSO and oxalyl chloride
(e)DMP(periodinane)reagent
Alcohols combine with ketones and aldehydes to form interesting derivatives, which we will discuss in Chapter 18. The following reactions show the hydrolysis of two such derivatives. Propose mechanisms for these reactions.
(a)
(b)
We have covered several oxidants that use a multi-valent atom (Cr, Cl, S, or I) as their active species, going from a higher oxidation state before the oxidation to a lower oxidation state after oxidizing the alcohol. Draw the structure of the following atoms, before and after the oxidation of an alcohol to a ketone or aldehyde. How many bonds to oxygen does each atom have before and after the oxidation?
(a) the Cr in chromic acid
(b) the Cl in sodium hypochlorite
(c) the S in the Swern oxidation
(d) the I in the DMP reagent
(e)the carbinol C in the alcohol that is oxidized.
Some alcohols undergo rearrangement or other unwanted side reactions when they dehydrate in acid. Alcohols may be dehydrated under mildly basic conditions using phosphorus oxy-chloride (POCl3) in pyridine. The alcohol reacts with phosphorus oxychlorides much like it reacts with tosyl chloride (Section 11-5), displacing a chloride ion from phosphorus to give an alkyl dichlorophosphate ester. The dichlorophosphate group is an outstanding leaving group. Pyridine reacts as a base with the dichlorophosphate ester to give an E2 elimination. Propose a mechanism for the dehydration of cyclohexanol by POCl3 in pyridine.
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