Which compound in each of the following pairs will react faste in S 2 reaction with OH ?(a) CH Br or CH I(b) (CH ) CCl or CH Cl
Question
Which compound in each of the following pairs will react faste in S 2 reaction with OH ?(a) CH Br or CH I(b) (CH ) CCl or CH Cl
Solution
In an S_N2 reaction, the rate of reaction depends on two factors: the strength of the leaving group and the steric hindrance of the substrate.
(a) CH3Br or CH3I: In this case, the leaving group is either Br- or I-. Iodide ions (I-) are better leaving groups than bromide ions (Br-) because they are larger and can stabilize the negative charge better. Therefore, CH3I will react faster in an S_N2 reaction with OH-.
(b) (CH3)3CCl or CH3Cl: Here, the factor to consider is the steric hindrance of the substrate. (CH3)3CCl is more sterically hindered than CH3Cl because it has more bulky methyl groups attached to the carbon that is bonded to the leaving group. S_N2 reactions prefer less sterically hindered substrates because the nucleophile can attack the substrate more easily. Therefore, CH3Cl will react faster in an S_N2 reaction with OH-.
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