In the aqueous solvolysis of compound 1 which species is the thermodynamically m

ID: 923330 • Letter: I

Question

In the aqueous solvolysis of compound 1 which species is the thermodynamically most stable reactive intermediate? What is the major substitution product of the aqueous solvolysis of compound 1? What is the major elimination product of the aqueous solvolysis of compound 1? What is the major product obtained from the S_N 2 reaction of compound 1 with sodium hydroxide in water? What is the major product resulting from the elimination reaction of compound 1 with potassium hydroxide? What is the major product resulting from the elimination reaction of compound 1 with potassium t-butoxide?

Explanation / Answer

Q18) During solvolysis , carbocation is formed as an intermediate. The initially formed carbocation is structrue number 2 which undergoes 1,2 hydride shift to give the structure number 3 as the more thermodynamically stable reactive intermediate. The structure number 2 is a secondary carbocation but structure number 3 is a tertiary benzylic carbocation which is stabilized by both inductive and resonance effects.

Q19) During the aqueous solvolysis , carbocation is the intermdiate which is planar. thus the nucelophile water can attack from both sides thus leading to a racemic modification. thus the product is structure number 18 in which the stereochemistry of the product is not defined, alternatively it is a mixture of structures 17 and 19.

Q20) In aqueous solvolysis , th elimination also follows E1 mechanism, thus the product of elimination is the Saytzeff (more substituted) and predominantly E- isomer. Thus structure number 10 is the answer.

Q21) If the reaction proceeds by SN2 mechanism , there is no formation of reactive intermediate and the sterochemistry is always inverted configuration due to back side attack of the nucleophile. Thus the answer is compound number 9.

Q22) Elimination with a small base like OH leads to Saytzeff (more substituted ) product and during dehydrohalogenation the product is cis alkene from meso/erythro isomers and trans alkene from racemic/threo isomers.The stereochemical requirement for E2 elimination is the leving group and hydrogen should be anti periplanar .

Here the starting compound is threo thus trans alkene is fromed. and the hydrogen on carbon number 4 is antiperiplanar to it thus the product formed is compound number 13.

Q23) Though E2 with a bulky base can giveHoffmann( less substituted alkene ) as major product, in the given compound 1 , thereis no such possibility. Thus the product is same compound number 13.

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In the aqueous solvolysis of compound 1, which species is the thermodynamically

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In the aqueous solvolysis of compound 1 which species is the thermodynamically m

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