Chapter 21: 1P (page 817)
Rank the following compounds in order of increasing reactivity towards nucleophilic attack.

Short Answer

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Chapter 21: 1P (page 817)
Rank the following compounds in order of increasing reactivity towards nucleophilic attack.


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Brevicomin, the aggregation pheromone of the western pine bark beetle, contains a bicyclic bridged ring system and is prepared by the acid-catalyzed cyclization of 6,7-dihydroxynonan-2-one.
a. Suggest a structure for brevicomin.
b. Devise a synthesis of 6,7-dihydroxynonan-2-one from 6-bromohexan-2-one. You may also use three-carbon alcohols and any required organic or inorganic reagents.

Treatment of (HOCH2CH2CH2CH2)2CO with acid forms a product of molecular formula C9H16O2and a molecule of water. Draw the structure of the product and explain howit is formed.
Devise a synthesis of each compound from cyclohexene and organic alcohols. You may use any other required organic or inorganic reagents
a)

b)

What alkene would yield 2,2-dimethoxycyclopentane-1,3-dicarbaldehyde on treatment withfollowed by ?

What 1° amine and carbonyl compound are needed to prepare each imine?
a.

b.

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