3. Both 2-chloro-2-methylpropane and 2-chloropropane hydrolyze with aqueous sodium hydroxide to generate 2-methyl-2-propanol and 2-propanol, respectively. i. Draw the bond-line formula of 2-chloro-2-methylpropane and 2- chloropropane. ii. It is known that the hydrolysis of 2-chloro-2-methylpropane and 2- chloropropane undergo with different mechanisms, draw the reaction mechanisms of the above two reactions. 111. With the use of reaction mechanism, explain why concentrated hydrochloric acid is added to 2-methyl-2-propanol and 2-propanol at room temperature, only 2-methyl-2-propanol will react.

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3. Both 2-chloro-2-methylpropane and 2-chloropropane hydrolyze with aqueous
sodium hydroxide to generate 2-methyl-2-propanol and 2-propanol, respectively.
Draw the bond-line formula of 2-chloro-2-methylpropane and 2-
i.
chloropropane.
ii.
It is known that the hydrolysis of 2-chloro-2-methylpropane and 2-
chloropropane undergo with different mechanisms, draw the reaction
mechanisms of the above two reactions.
iii.
With the use of reaction mechanism, explain why concentrated
hydrochloric acid is added to 2-methyl-2-propanol and 2-propanol at room
temperature, only 2-methyl-2-propanol will react.
Transcribed Image Text:3. Both 2-chloro-2-methylpropane and 2-chloropropane hydrolyze with aqueous sodium hydroxide to generate 2-methyl-2-propanol and 2-propanol, respectively. Draw the bond-line formula of 2-chloro-2-methylpropane and 2- i. chloropropane. ii. It is known that the hydrolysis of 2-chloro-2-methylpropane and 2- chloropropane undergo with different mechanisms, draw the reaction mechanisms of the above two reactions. iii. With the use of reaction mechanism, explain why concentrated hydrochloric acid is added to 2-methyl-2-propanol and 2-propanol at room temperature, only 2-methyl-2-propanol will react.
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