Question

4)Draw stepwise mechanism that will explain the products of the following reaction.

5)draw the rate law and the transition state for the following reaction

6)what starting material would exclusively give you the product shown? Draw the mechanism using a chair structure.

4) Draw a stepwise mechanism that will explain the products of the following reaction on the back of this page. (6 points) 5) Draw the rate law and the transition state for the following reaction: (4 pts) DMSO CH;CH CH2Cl + NaCN 6) What starting material would exclusively give you the product shown? Draw the mechanism using a chair structure: (8 pts) CH(CH3)2 NaOCHICHI CHCH-он (only E2product

Answer 1

DMSO CH3CH2CH2CI NaCN CH3CH2CH2CN Reaction is follows the SN2 mechanism. Therefore, the rate of rection is dependent on both the rectant. DMSO is used as a solvent for rection K [CH3CH2CH2CI [CN] Rate Step 1- Heterolysis of C-I bond Step 2- Methyl group shift along with bond pair electron to generate tertiary carbocation, Step 3- Attack of chloride on carbocation to form a product C(CH3)2 C(CH3)2 NaOCH2CH3 CH3CH20H Hас Нас Br Br For E2 elimination reaction, the proton and leaving group has to be in diaxial position as shown above. C(CH3)2 C(CH3)2 NaOCH2CH3 CH3CH20H Br Нас Hас Br Н Unexpected but more stable product according to zetsev's rule. EtO