1. Which nucleophilic substitution reaction is not likely to occur? 2. And which

Question

1. Which nucleophilic substitution reaction is not likely to occur? 2. And which one is likely to occur?

Though answers are marked, please provide explanaitons.

12) Waic nuckphc nt A)I CH3CH2 Cl B)I CH3CH2-BrCH3CH-I Br c)r + CH,CH2 OH CH3CH2-OCH3 Br 13) Which nucleophilic substitution reaction would be likely to occur (although probably not in excellent yield, due to competing elimination)? A) HO+ CH3CH2CH2CHICH3 D) All of these choices are likely to occur. E) None of these choices are likely to occur

Explanation / Answer

1) The nucleophilicity order of the species/ions is

I- > Br-> Cl-

and Ch3O- > OH-> halide ions.

The halide ions are more nucleophilic than basic , thus with them the major reaction is substitution.

While the CH3O- and OH - are strong nucleophiles as well as strong bases .

the CH3S- is only nucleophilic and very weak base.

12) Thus in the first (12) question a weaker nucleophile like I- can not replace stronger nucleophile OH- , thus option C is most unlikely to occur.

Q13)

Here by the same analogy we see in option A

a stronger nucleophile/base OH- replacing a weaker nucleophile I- easily.

In the other two options a weaker Nucleophile Cl- can not replace stronger Nu/base OH- .

weak base SCH3 does not substitute stronger OCh3.

Thus option A is correct.

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