based on the sn1 reaction with AgNO3 use the table below to answer the following

Question

based on the sn1 reaction with AgNO3 use the table below to answer the following questions:

1.) looking at entries 11, 14 and 16, what conclusion can you draw about the type of alkyl chloride employed (primary, secondary or tertiary) and the rate at which the sn1 reaction occurs? explain why this might be.
2.) looking at entries 12, 15 and 17, is the trend the same or different with the alkyl bromides? does this result make sense?
3.) comparing the trend within entries (11, 12, 13), (14 vs. 15) and (16 vs. 17), what can you say about the type of alkyl halide used and the rate of the reaction? explain this.
4.) comparing entries 11 and 19, is there a difference in the rates? if there is, explain why there is a difference in the rate. hint: think about the intermediates involved
5.) comparing entries 14 and 18, is there a difference in the rates? should there be?

mplele the table below. For the relaivly 1e reactive. f Alky Relative of Halide Reactivity Halide Relative Entry Alkyl Halide Compound 2, or 3) 11 | 1-chlorobutane |/ 12 | 1-bromobutane |/N/er Alkyl Halide Line Structure of Type of Alky 2 or3) Reactivity 13 | |(// 1-iodobutane 14 2-chlorobutane 15 2-bromobutane 16 2-chloro-2- methylpropane 17 2-bromo-2 methylpropane | ! O-e! 18 chlorocyclohexane 19 allyl chloride

Explanation / Answer

1) 11 is a primary halide,14 is a secondary halide and 16 is a tertiary halide. In SN1 reaction a carbocation is formed as intermediate. greater the stability of the carbocation greater will be the rate of the reaction. The sbality of carbocation follows the order 3^o>2^o>1^o. So, the reaction will be fastest in case of 16, followed by 14 and least will be 11. Hence, the rate of SN1 reaction follows the order 3^o>2^o>1^o alkyl halide.

2) This trend is similar in case of alkyl bromide . Rate follows the order : 3^o>2^o>1^o

3) Comparing the trends, it is clear that SN1 reaction rate is faser with -Br as leaving group. This is because -Br is a better leaving group than -Cl. Iodide is even better leaving group. the order of leaving group ability in halides is : I->Br->Cl-. This is because as the size increases from Cl to I, C-halogen bond becomes weaker and easier to break.

4) the intermediate (carbocation) formed is resonance stabilized in case of 19. So, the reaction rate is faster.

5) There is no difference in rate as both are primary halide.

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