Under SN1 conditions the hydrolysis o neo-pentyl bromide gives

Question

Under SN1 conditions the hydrolysis o neo-pentyl bromide gives (A)  CH3- underset beginsmallmatrix | CH3 endsmallmatrix mathopC =CH-CH2OH  (B)  CH3- underset beginsmallmatrix | OH endsmallmatrix overset beginsmallmatrix CH3 | endsmallmatrix mathopC -CH2CH3  (C)  CH3- underset beginsmallmatrix | CH3 endsmallmatrix overset beginsmallmatrix CH3 | endsmallmatrix mathopC -CH2OH  (D) None of the above

Tardigrade Admin · Accepted Answer

xrightarrow[]1,2-Me shiftCH3- underset beginsmallmatrix (3o)carbocation (more stable) endsmallmatrix mathop underset⊕ overset beginsmallmatrix CH3 | endsmallmatrix mathopC overset beginsmallmatrix CH3 | endsmallmatrix mathop-CH2 xrightarrow[]OH-CH3- underset beginsmallmatrix (3o)carbocation (more stable) endsmallmatrix mathop underset⊕ overset beginsmallmatrix CH3 | endsmallmatrix mathopC overset beginsmallmatrix CH3 | endsmallmatrix mathop-CH2 xrightarrow[]OH-CH3- underset beginsmallmatrix | OH endsmallmatrix overset beginsmallmatrix CH3 | endsmallmatrix mathopC -CH2CH3

Q. Under $S_{N} 1$ conditions the hydrolysis o neo-pentyl bromide gives

$C H_{3} - ∣ C H_{3} C = C H - C H_{2} O H$

$C H_{3} - ∣ O H C C H_{3} ∣ - C H_{2} C H_{3}$

$C H_{3} - ∣ C H_{3} C C H_{3} ∣ - C H_{2} O H$

None of the above

$1, 2 - M e s hi f t C H_{3} - (3^{o}) c a r b oc a t i o n (m ore s t ab l e) \oplus C C H_{3} ∣ - C H_{2} C H_{3} ∣$ $O H^{-} C H_{3} - (3^{o}) c a r b oc a t i o n (m ore s t ab l e) \oplus C C H_{3} ∣ - C H_{2} C H_{3} ∣$ $O H^{-} C H_{3} - ∣ O H C C H_{3} ∣ - C H_{2} C H_{3}$

Q. Under SN​1 conditions the hydrolysis o neo-pentyl bromide gives

CH3​−∣CH3​​C​=CH−CH2​OH

CH3​−∣OH​CCH3​∣​​−CH2​CH3​

CH3​−∣CH3​​CCH3​∣​​−CH2​OH