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underset ((X)) underset ("Optically acti...

`underset ((X)) underset ("Optically active") (C_5 CH_(13)N) underset (N_2)overset(NaNO_2//HCl) rarr (Y)underset (+" Other product" ) ("Tertiary alcohol")`
Find (X ) and (Y ) . Is (Y ) optically active ? Write the intermediate steps .

Text Solution

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Step 1. To determine the structure of compound (X)
(i) Since compound (x) on treatment with `NaNO_(2)//HCl` evolves `N_(2)` gas, therefore, (X) must be a primary amine. Further since compound (X) is optically active, therefore, it must e contain a chiral carbon. Now `NH_(2)` group cannot be directly attached to the chiral carbon since such amines readily undergo racemization due to nitrogen inversion. therefore, the structure of the compound X is
`underset("2-Methylbutanamine (X) (optically active)")(CH_(3)CH_(2)-overset(CH_(3))overset(|)(.^(**)C)H-CH_(2)NH_(2))`
Step 2. To determine the structure of tertiary alcohol (X)
The formation of compound (Y) from compound (X) may be explained as follows:

Thus, the compound (Y) is 2-methylbutan-2-ol. it is optically inactive.
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