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Question

(C) The reaction involves the nucleophilic substitution of a primary alkyl halide in the presence of $NaCN$ and $DMF$ (a polar aprotic solvent), which

Vedclass · Accepted Answer

$2-$($3$-iodophenyl)acetonitrile

Vedclass · Answer

(C) The reaction involves the nucleophilic substitution of a primary alkyl halide in the presence of $NaCN$ and $DMF$ (a polar aprotic solvent), which favors the $S_{N}2$ mechanism.The substrate contains two halogen atoms: an iodine atom directly attached to the benzene ring (aryl iodide) and a chlorine atom attached to a benzylic carbon (benzylic chloride).$1$. The $C-I$ bond attached to the benzene ring has partial double-bond character due to resonance, making it very resistant to nucleophilic substitution.$2$. The benzylic $C-Cl$ bond is highly reactive towards $S_{N}2$ substitution because the transition state is stabilized by the adjacent benzene ring.Therefore, the $CN^-$ nucleophile selectively attacks the benzylic carbon, displacing the $Cl^-$ ion to form $2-(3-iodophenyl)acetonitrile$ as the major product.

The major product of the following reaction is:

Similar Questions

The correct decreasing order of $SN^2$ reactivity of the following alkyl halides is:
$(I)$ $CH_2=CH-Br$
$(II)$ $CH_3-Br$
$(III)$ $CH_3-CH(Br)-CH_3$
$(IV)$ $CH_3-CH_2-Br$

Consider the reaction: $CH_3-CH_2-CH(F)-CH_3 \xrightarrow{CH_3O^{-}} X$. The alkene formed in major amount is:

What is $E$?
Cyclohexanone $\xrightarrow{Br_2 + CH_3COOH} A$ $\xrightarrow{Alc. KOH} B$ (Product with six-membered ring) $\xrightarrow[(2) H_2O]{(1) CH_3MgBr} C$ $\xrightarrow{H^{\oplus} + \Delta} D$ $\xrightarrow{HBr (1 \text{ mole})} E$

Choose the halogen which is most reactive towards $SN1$ reaction in the given compounds $(A, B, C, D)$:

What is the product formed when chloroform reacts with concentrated $HNO_3$?

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