Chapter 11: Q53P (page 589)
Give the structures of the intermediates and products V through Z.
Chapter 11: Q53P (page 589)
Give the structures of the intermediates and products V through Z.
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Get started for freeSuggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent
(a) butan - 1 - ol → butanal, CH3CH2CH2CHO
(b) but - 2 - en - 1 - ol → but - 2 - enoic acid, CH3CH = CHCOOH
(c) butan - 2 - ol → butan - 2 - one, CH3COCH2CH3
(d) cyclopentanol → 1 - cyclopentylpropan - 1 - ol (twosteps)
(e) cyclopentyclohexanol → 2 - methylcyclohexanone (several steps)
(f) 1 - methylcyclohexanol → 2 - methylcyclohexanone (several steps)
Two products are observed in the following reaction.
(a) Suggest a mechanism to explain how these two products are formed.
(b) Your mechanism for part (a) should be different from the usual mechanism of the reaction of SOCl2 with alcohols. Explain why the reaction follows a different mechanism in
this case.
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 reactions of the following compounds with:
(1) chromic acid or excess sodium hypochlorite with acetic acid.
(2)PCC or NaOCl (1 equivalent) with TEMPO.
(a)cyclohexanol (b)1-methylcyclohexanol
(c)cyclopentylmethanol (d)cyclohexanone
(e)cyclohexane (f)1-phenylpropan-1-ol
(g)hexan-1-ol (h)acetaldehyde, CH3CHO
Neopentyl alcohol, (CH3)3CCH2OH, reacts with concentrated HBr to give 2-bromo-2-methylbutane, a rearranged product. Propose a mechanism for the formation of this product.
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