We have seen that the S_N2 reaction of ethyl bromide (1) and iodide proceeds via

Question

We have seen that the S_N2 reaction of ethyl bromide (1) and iodide proceeds via transition state 3 to furnish the products ethyl iodide (4) and bromide, Eq. (1). We argued that the vector of I addition was defined by the large lobe on sigma*_c_Br' as indicated. However, this same LUM O cr*_c_Br appears to have a large lobe at the back end of the bromine atom, suggesting that TS 6 should be considered as well, Eq. (2). Using the following values as input data, calculate the delta G for Eq. (2) as written. BDEs (kcal/mol): H_3CCH_2-Br (68), H-l (71), l-Br (42), H_3CCH_2-H (98).pK_as:H_3CCH_2-H (60), HI (-10).

Explanation / Answer

Using the bond energies given above the dG for reaction 2 would be,

b. -97 kcal/mol

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