91Ó°ÊÓ

Rank the following compounds in order of increasing reactivity towards nucleophilic attack.

What starting materials are needed to prepare each alkene by a Wittig reaction? When there are two possible routes, indicate which route, if any, is preferred.

a.

b

c.

Show two methods to synthesize each alkene: a one-step method using a Wittig reagent, and a two-step method that forms a carbon–carbon bond with an organometallic reagent in one of the steps.

a.

b.

¶Ù°ù²¹·É t³ó±ð p°ù´Ç»å³Ü³¦³Ù f´Ç°ù³¾±ð»å w³ó±ð²Ô C±á₃CH₂CH₂CH₂NH₂reacts with each carbonyl compound in the presence of mild acid.

a.

b.

c.

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

a.

b.

What two enamines are formed when 2-methylcyclohexanone is treated with (CH₃)₂NH?

What carbonyl compound and amine are formed by the hydrolysis of each compound?

a.

b.

c.

Draw a stepwise mechanism for the following imine hydrolysis

Which compound in each pair forms the higher percentage of gem-diol at equilibrium?

a.

or

b.

or

Draw a stepwise mechanism for the following reaction