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1. why does benzyl bromide react under both Sn1 conditions and Sn2 conditions? 2. To promote...

1. why does benzyl bromide react under both Sn1 conditions and Sn2 conditions?

2. To promote the Sn1 mechanism we used AgNO3 in a polar, protic solvent. True or False? Why?

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Q1. SN2 mechanism is prefered by primary alkyl halids and SN1 is prefered by the substances which form a stable carbocation. Benzyl bromide is a primary alkyl halide and will show SN2 substitution. However benzyl bromide can form a stable carbocation as well upon loss of bromide anion. The benzyl cation is resonance stabelised. Hence Benzyl bromide can show both SN1 as well as SN2 pathways.

Q2. The proposition is true. Ag+ coordinates with halide ion facilitating the formation of carbocation. Further polar protic solvent will favour SN1 mechanism by stabelising the carbocation.

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