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SN2 conditions SN1 conditions 2-Chlorobutane 10:42 min 8:16.34 min 2-Bromobutane

ID: 541191 • Letter: S

Question

SN2 conditions SN1 conditions 2-Chlorobutane 10:42 min 8:16.34 min 2-Bromobutane 5:39 min 7.28 s 1-Chlorobutane 6:21 min 7:05 min 1-Bromobutane 1.66 s 1:20.56 min 2-chloro-2-methylpropane 6:13 min 0.36s crotyl chloride 12.85 s 8.36s benzyl chloride 37.86 s 1:14 min bromobenzene no reaction no reaction Questions to Answer Cm answer Inter 1. Under Sn2 conditions, does your data support that 1s2-3? 2. Under SN1 conditions, does your data support that 352S17 3. How can you explain that crotyl chioride and benzyl chloride reacted so quickly under Sy1 conditions? Which is a better leaving group, Cl or Br? 4.

Explanation / Answer

1. Yes For SN2 reactions 1o>2o>3o alkyl halide ( 1-chlorobutane 1-bromo butane SN2 reactions are fast).

2. Yes For SN1 reactions 3o > 2o > 1o alkyl halide ( 2-chloro-2-methylpropane and crotyl chloride SN1 reactions are fast).

3. Crotyl chlordie is forming allyl carbocataion which is resonance stabilized after loss of chloride anion and benzyl chloride is forming benzyl cataion which is also resonance stabilized after loss of chloride ion. Because of resonance stabilization cataions the SN1 reactions are fast.

4. Bromine is good leaving group than chlorine.