Experiment for SN1 reactions in silver nitrate/ethanol. 1. 1-chlorobutane 2. 1-b

Question

Experiment for SN1 reactions in silver nitrate/ethanol.

1. 1-chlorobutane

2. 1-bromobutane

3. 2-chlorobutane

4. 2-bromobutane

5. bromocyclohexane

6. 2-chloro-2-methylpropane (t-butyl chloride)

7. crotyl chloride

8. benzyl chloride (-chlorotoluene)

Questions: (please and thank you!)

2) Address the following questions for Part 2 (silver nitrate/ethanol):

a) (1 point) How do the choice of reagents favor the SN1 reaction?

b) (1 point) When comparing 1°, 2°, and 3° alkyl halides, what is the expected trend in reaction

rate? List in order of most reactive to least reactive.

c) (2 points) Do the structures of the reactive, moderately reactive, and unreactive alkyl halides

correlate with their reactivity? Discuss briefly.

d) (2 points) Why are benzyl chloride and crotyl chloride more reactive than a typical primary alkyl

chloride? (Hint: what is special about the carbocation formed?)

Explanation / Answer

a) The nucleophile should be somewhat weak, so that it allows the formation of the carbocation before attacking. Thus, a reagent which provides a weak nucleophile should be selected.

b) 30>20>10

c) Yes. For example consider benzyl chloride and t-butyl chloride. T-butyl chloride reacts rapidly because it is a tertiary alkylhalide. However, 1-chlorobutane is unreactive as its structure inhibits the formation of a carbocation.

d) The carbocations formed are resonance stabilized.

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