Draw the product(s) that are expected when tert-butyl bromide undergoes solvolysis in isopropanol, (CH3)2CHOH.

Chemistry

2 answers:

N76 [4]3 years ago

5 0

Those reactions in which Alkyl Halide reacts with the solvent without the involvement of any acid or base is called as Solvolysis. In given problem <em>tert</em>-Butyl Bromide is a tertiary Alkyl Halide and we know well that tertiary alkyl halides undergo SN¹ and E¹ elimination reaction due to the formation of stable tertiary carbocation. In given example after the formation of carbocation when Isopropyl act as nucleophile it will produce ether and when it acts as a base it will produce unsaturated compound. The reaction along with both products is shown below,

Novay_Z [31]3 years ago

4 0

The product forms are $\boxed{{\text{2 - isopropxy2 - methylpropane and 2 - methylprop1 - ene}}}$ . (Refer to image attached ).

Further explanation:

Solvolysis is a chemical reaction in which the solvent, such as water or alcohol, is one of the reagents. At high temperatures or in the presence of strong bases, some solvents act as eliminating agents, producing alkenes from alkyl halides.

SN1 reactions are nucleophilic substitution reactions that involve a nucleophile that can replace a leaving group from the substrate. SN1 reactions are unimolecular. Also, the rate of this reaction depends only on the concentration of one reactant. Sn1 reaction forms stable tertiary carbocation.

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule. The removal of substituent results in the formation of a double bond. The reaction proceeds through a carbocation intermediate.

Tert-butyl bromide is a tertiary alkyl halide. The tertiary alkyl halides undergo SN1 and E1 reactions due to the formation of a stable tertiary carbocation. It reacts with isopropanol under solvolysis to form ether and a double bond compound.

The solvolysis reaction between tert-butyl bromide and isopropanol is as follows:

${\text{tert - butylbromide}} + {\text{isopropanol}} \to {\text{2 - isopropxy2 - methylpropane}} + {\text{2 - methylprop1 - ene}}$ .

Hence, the product forms by solvolysis of tert-butyl bromide in isopropanol are ${\mathbf{2 - isopropxy - 2 - methylpropane}}$ and ${\mathbf{2 - methylprop - 1 - ene}}$