Chloropentane and Hydroxide Reaction Discussion

 

  1. What product results from the SN2 reaction between (R)- 2- chloropentane and hydroxide?

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  1. Provide a detailed, stepwise mechanism for the reaction below.

(CH3)2CHCH2CH2CH2I + CN- (CH3)2CHCH2CH2CH2CN + I-

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  1. Provide the product which results when (S)- 2- iodopentane is treated with KCN in DMF.

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  1. Provide the major organic product(s) in the reaction below.

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  1. Provide the major organic product(s) in the reaction below.

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  1. Provide the major organic product(s) in the reaction below.

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  1. Provide the structure of the major organic product of the following reaction.

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  1. Provide the structure of the major organic product of the following reaction.
  2. Provide the structure of the major organic product of the following reaction.

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  1. Rank the species below in order of increasing nucleophilicity in protic solvents: CH3CO2- , CH3S- , HO- , H2O.

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  1. In each of the pairs below, which is the best nucleophile in alcoholic solvents?
  2. CH3S- or CH3O-
  3. (CH3)2NH or (CH3)3N
  4. Cl- or F-
  5. SCN- or OCN-

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  1. word image 1669 Why, in a polar protic solvent, is iodide a better nucleophile than fluoride?

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  1. Provide the major organic product(s) of the reaction shown.

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  1. Provide the major organic product(s) of the reaction shown.

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  1. Give the mechanism.

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  1. Give the mechanism of the reaction shown below.

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  1. Provide the major organic product of the reaction below and a detailed, stepwise mechanism which accounts for its formation.

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  1. Provide the structure of the major organic products which result in the reaction below.

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  1. Provide the major organic product(s) in the reaction below.

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  1. Provide the major organic product(s) in the reaction below.

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  1. Provide the major organic product(s) of the reaction shown

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  1. Provide the major organic products(s) of the reaction shown:.

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  1. Draw the product for the following SN2 reaction.

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  1. Give the name(s) of the product(s) for the following SN2 reaction.

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  1. Provide the major organic product(s) in the reaction below.

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1) (S)- 2- pentanol

2)

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3)

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4)

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5)

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6)

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7)

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8)

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9)

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  1. H2O < CH3CO2- < HO- < CH3S-
  2. a. CH3S-
    1. (CH3)2NH
    2. Cl-
    3. SCN-
  3. 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)

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14)

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15)

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16)

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17)

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mechanism:

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18)

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19)

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20)

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21)

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22)

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23)

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24) (S)- 3- hexanol

25)

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