Question

Write equations for the reactions investigated. Label Sn1 or Sn2.

1)Butyl bromide in 15%NaI-acetone

2)Butyl bromide in 1%ethanolic silver nitrate

?????3)Butyl chloride in 15% NaI-acetone

4) Butyl chloride in 1% ethanolic silver nitrate

5)Sec-butyl chloride in 15%NaI-acetone

6) Sec-butyl chloride in 1% ethanolic silver nitrate

7) Tert-butyl chloride in 15%NaI-acetone

8) Tert-butyl chloride in 1% ethanolic silver nitrate

9) Crotyl chloride in 15% NaI-acetone

10) Crotyl chloride in 1% ethanolic silver nitrate

Any help would be appreciated! I will rate your response in return!

Answer 1

1)Butyl bromide in 15%NaI-acetone

C4H9 Br + NaI     ------ acetone----------------->       I- C4H9 + NaBr    (SN2)

2) Butyl bromide in 1%ethanolic silver nitrate

C4H9 Br + C2H5OH ---AgNO3-------------->C4H9OC2H5 + AgBr(ppt) + HNO3   (SN1)

3)Butyl chloride in 15% NaI-acetone

C4H9Cl + NaI     ------ acetone----------------->       Cl- C4H9 + NaCl    (SN2)

4) Butyl chloride in 1% ethanolic silver nitrate

C4H9Cl + C2H5OH ---AgNO3-------------->C4H9OC2H5 + AgCl(ppt) + HNO3   (SN1)

5)Sec-butyl chloride in 15%NaI-acetone

CH3 CH(Cl)-CH2-CH3 + NaI     ------ acetone-----------------> CH3 -CH(I)-CH2-CH3 + NaCl (SN2)

6) Sec-butyl chloride in 1% ethanolic silver nitrate

CH3 CH(Cl)-CH2-CH3 + C2H5OH -------AgNO3-------------->CH3 CH( C2H5O)-CH2-CH3 (SN1)

7) Tert-butyl chloride in 15%NaI-acetone

(CH3)3 C-Cl + NaI     ------ acetone-----------------> (CH3)3 C-I + NaCl (SN1)

8) Tert-butyl chloride in 1% ethanolic silver nitrate

(CH3)3 C-Cl + C2H5OH -------AgNO3-------------->(CH3)3 C-O-C2H5 + AgCl + HNO3 (SN1)

9) Crotyl chloride in 15% NaI-acetone

CH3-CH=CH-CH2-Cl + NaI     ------ acetone----------------->CH3-CH=CH-CH2-I + NaCl (SN2)

10) Crotyl chloride in 1% ethanolic silver nitrate

CH3-CH=CH-CH2-Cl + C2H5OH -------AgNO3-------------->CH3-CH=CH-CH2-OC2H5 + AgCl (SN2)

EXPLANATION

All these reactions based two important concepts

SN2 reaction in the SN2 reaction alkyl halides order of reactivity   3⁰ RX   > 2⁰ RX > 1⁰ RX

and non-polar solvents are favourable for SN2. so NaI + acetone involved all reactions are maximum SN2 . because here acetone non-polar solvent . except one case in case of tertiary butyl bromide SN1 takes place reason steric hindrance of alkyl groups

SN1 reactions in the SN1 reaction alkyl halides order of reactivity   3⁰ RX <   2⁰ RX   < 1⁰ RX

polar solvents are more favourable for SN1. so ethanol is polar. AgNO3 + ethanol mixer give SN1