Chapter 11: Q18P (page 560)
Write balanced equations for the three preceding reactions.
Short Answer
(a)

(b) 
(c)
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Chapter 11: Q18P (page 560)
Write balanced equations for the three preceding reactions.
(a)

(b) 
(c)
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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.
Under normal circumstances, tertiary alcohols are not oxidized. However, when the tertiary alcohol is allylic, it can undergo a migration of the double bond (called an allylic shift) and subsequent oxidation of the alcohol. A particularly effective reagent for this reaction is Bobbitt’s reagent, similar to TEMPO used in many oxidations. (M. Shibuya et al., J. Org. Chem., 2008, 73, 4750.)

Show the expected product when each of these 3° allylic alcohols is oxidized by Bobbitt’s reagent.
(a)

(b)

(c)

(d)

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

Two unknowns, X and Y, both having the molecular formula C4H8O , give the following results with four chemical tests. Propose structures for X and Y consistent with this information.
Bromine | Na metal | Chromic acid | Lucas reagent | |
Compound X | decolorizes | Bubbles | orange to green | no reaction |
Compound Y | no reaction | no reaction | no reaction | no reaction |
Give the structures of the intermediates and products V through Z.

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