Question

1. The following reaction is run twice. It is run once with methanol as the solvent, and once with dimethylsulfoxide (DMSO) as the solvent. The products of the two reactions are analysed and have their optical rotations measured. Using one set of reaction conditions the optical rotation is zero. Under the other set of reaction conditions the optical rotation is [?] = -25. Other than optical rotation all other analyses point to the same product. Using your knowledge of nucleophilic substitution reactions explain why there are different outcomes by showing the possible reaction mechanisms. Which solvent matches which product? (R) - 2- bromobutane [?] = +24 2. For each of the following pairs indicate the best and explain: a) best leaving group i) CH3CH2Cl vs CH3CH2OTf ii) CH3CH2CH2Br vs CH3CH2CH2OH b) best nucleophile i) ii) CH3NH2 vs CH3NHCH3

          1. The following reaction is run twice. It is run once with methanol as the solvent, and once with dimethylsulfoxide (DMSO) as the solvent. The products of the two reactions are analysed and have their optical rotations measured. Using one set of reaction conditions the optical rotation is zero. Under the other set of reaction conditions the optical rotation is [?] = -25. Other than optical rotation all other analyses point to the same product. Using your knowledge of nucleophilic substitution reactions explain why there are different outcomes by showing the possible reaction mechanisms. Which solvent matches which product?

(R) - 2- bromobutane
[?] = +24

2. For each of the following pairs indicate the best and explain:
a) best leaving group
i) CH3CH2Cl vs CH3CH2OTf
ii) CH3CH2CH2Br vs CH3CH2CH2OH
b) best nucleophile
i)
ii) CH3NH2 vs CH3NHCH3

1. The following reaction is run twice. It is run once with methanol as the solvent, and once with dimethylsulfoxide (DMSO) as the solvent. The products of the two reactions are analysed and have their optical rotations measured. Using one set of reaction conditions the optical rotation is zero. Under the other set of reaction conditions the optical rotation is [?] = -25. Other than optical rotation all other analyses point to the same product. Using your knowledge of nucleophilic substitution reactions explain why there are different outcomes by showing the possible reaction mechanisms. Which solvent matches which product?

(R) - 2- bromobutane
[?] = +24

2. For each of the following pairs indicate the best and explain:
a) best leaving group
i) CH3CH2Cl vs CH3CH2OTf
ii) CH3CH2CH2Br vs CH3CH2CH2OH
b) best nucleophile
i)
ii) CH3NH2 vs CH3NHCH3

Added by James F.

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