Exam 1 I. For the following statements indicate which mechanism (SNI andor s 2)

Question

Exam 1 I. For the following statements indicate which mechanism (SNI andor s 2) the following 12 pts would support. The rate of the reaction was when the nucleophile was increased The rate of the reaction was increased when the substrate was increased in the presence anaproti The rate of the reaction in the presence of a po The the was increased Cl The reaction involves a The product shows inversion of configuration. [8 pts) 2. Circle the stronger Nucleophile in DMso: CH3OH or CHJO b, NH2 or OH c, CH COO or CHyo d. CH or (CHyS determine which position will react faster 3. For answer. [6 pts) under SN1 or SN2 conditions and explain your 4. Write a CoMPLETE mechanism for the following reaction, draw the product and [10 pts) indicate the rate determining step. HCI H20 OH

Explanation / Answer

(1)

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(i) SN1 mecahnism is two step mecahnism.

(ii) Firs t step involes the formation carbocation intermedaite.

(iii) It is slow and rate determining step which involves only alkyl halide.

(iv) Rate = k[Alkylhalide]

(v) It forms the racemic mixture of products with the chiral substrate.

(vi) Since carbocation is formed as intermediate, this mecahnism is favored by polar protic solvents that stabilise the intermediate.

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(i) SN2 mecahnism is a concerted mechanism.

(ii) It occurs in single step where the attacking nucleophile attactks the carbon and the old nucleophile leaves the carbon simultaneously.

(iii) So, rate of reaction depends on both alkyl halide and nucleophile.

Rate = k[RX][Nucleophile]

(iv) The product has inversion of configuration becuase the new nucleophile attacks the carbon from back side of the old nucleophile.

(v) SInce no cahrged intermediate is being formed it is favored by aprotic solvents.

Now the given statements,

(a) SN2

(b) Both

(c) SN2

(d) SN1

(e) SN1
(f) SN2

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