S 2 iodopentane is treated with kcn in dmf

Ch 8-homework 1) What product results from the SN2 reaction between (R)-2-chloropentane and hydroxide? 2) Provide a detailed, stepwise mechanism for the reaction below. (CH3 )2 CHCH2 CH2 CH2I + CN- (CH3 )2 CHCH2 CH2 CH2 CN + I3) Provide the product which results when (S)-2-iodopentane is treated with KCN in DMF. 4) Provide the major organic product(s) in the reaction below. 5) Provide the major organic product(s) in the reaction below. 6) Provide the major organic product(s) in the reaction below. 7) Provide the structure of the major organic product of the following reaction. 8) Provide the structure of the major organic product of the following reaction. 1 9) Provide the structure of the major organic product of the following reaction. 10) Rank the species below in order of increasing nucleophilicity in protic solvents: CH3CO2 - , CH3 S- , HO- , H2 O. 11) In each of the pairs below, which is the best nucleophile in alcoholic solvents? a. b. CH3 S- or CH3 O(CH3 )2 NH or (CH3 )3 N c. d. Cl- or FSCN- or OCN- 12) Why, in a polar protic solvent, is iodide a better nucleophile than fluoride? 13) Provide the major organic product(s) of the reaction shown. 14) Provide the major organic product(s) of the reaction shown. 15) Give the mechanism. 2 16) Give the mechanism of the reaction shown below. 17) Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation. 18) Provide the structure of the major organic products which result in the reaction below. 19) Provide the major organic product(s) in the reaction below. 20) Provide the major organic product(s) in the reaction below. 21) Provide the major organic product(s) of the reaction shown 3 22) Provide the major organic products(s) of the reaction shown:. 23) Draw the product for the following SN2 reaction. 24) Give the name(s) of the product(s) for the following SN2 reaction. 25) Provide the major organic product(s) in the reaction below. 4 Answer Key Testname: CH08-ANSWER 1) (S)-2-pentanol 2) 3) 4) 5) 6) 7) 8) 9) 10) H2 O < CH3 CO2 - < HO- < CH3 S- 5 Answer Key Testname: CH08-ANSWER 11) a. b. CH3 S(CH3 )2 NH c. Cld. SCN12) In addition to iodide being more polarizable due to its larger size, the fluoride ion is more highly solvated which retards its ability to function as a nucleophile. 13) 14) 15) 16) 6 Answer Key Testname: CH08-ANSWER 17) mechanism: 18) 19) 20) 21) 22) 7 Answer Key Testname: CH08-ANSWER 23) 24) (S)-3-hexanol 25) 8 ...
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