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Magazine Chapter 11: Q46P (page 588)
Show how you would convert (S)-heptan-2-ol to
(a) (S)-2-chloroheptane.
(b) (R)-2-bromoheptane.
(c) (R)-heptan-2-ol.
Short Answer
(a)
(b)
(c)
Step by step solution
(a): Alcohol
Alcohol is a compound that contains a hydroxyl group. It is used in the spirits.
Heptan-2-ol is used as a flotation agent for the processing of ore. TheHydroxyl group is attached to the second carbon of the heptane compound.
Conversion
(S)-Heptan-2-ol is treated with SOCl2 to form (S)-2-chloroheptane.
Formation of (S)-2-chloroheptane
(b): Reagents
TsCl is used in treating primary alcohol as an activating group, and pyridine neutralizes hydrochloric acid generated from the reaction.
Conversion
(S)-Heptan-2-ol is treated with TsCl/pyridine forms (S)-heptane-2-tosylate, which on further reaction with forms (R)-2-bromoheptane.
Formation of (R)-2-bromoheptane
(c): Reagents role
TsCl is used in treating primary alcohol as an activating group, and pyridine neutralizes hydrochloric acid generated from the reaction.
Conversion
(S)-Heptan-2-ol is treated with TsCl/pyridine forms (S)-heptane-2-tosylate, which, on further reaction with sodium hydroxide, kept in the cold to avoid elimination and forms (R)-heptan-2-ol.
Formation of (R)-hepatan-2-ol
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