I think the most frequently asked question you have to know in Ochem is Sn1/Sn2/E1/E2. Does everybody agree?
It seems easy, but sometimes it's very tricky.
I have two questions here.
1. (CH3)3CCHBrCH3 + NaOH ---> ?
A. (CH3)3CCHOHCH3
B. (CH3)3CC=CH2
The answer is both A and B.
The reactant is secondary halide and nucleophie (NaOH) is strong base. According to the table in Kaplan lesson book p301, only E2 can occur. However, the solution said that depending on the condition, both Sn 2 and E2 can occur. I don't understand why. The conditions (secondary halide and strong base) are already given in the problem. On earth, which conditions does the solution refer?
2. Ar-CH2C(C2H5)CH3Cl + Br- ---> ?
A. Double bond formation
B. Loss of optical activity
The answer is B.
The problem gave tertiary halide and good nucleophile but weak base (Br-). According to the table in Kaplan lesson book p301, both E1 and Sn1 can occur. E1 means doulbe bond formation, and Sn 1 means loss of optical activity. So I think the answer can be both A and B. However, the solution said the answer is only B.
Can anybody explain the solution? Thank you~
It seems easy, but sometimes it's very tricky.
I have two questions here.
1. (CH3)3CCHBrCH3 + NaOH ---> ?A. (CH3)3CCHOHCH3
B. (CH3)3CC=CH2
The answer is both A and B.
The reactant is secondary halide and nucleophie (NaOH) is strong base. According to the table in Kaplan lesson book p301, only E2 can occur. However, the solution said that depending on the condition, both Sn 2 and E2 can occur. I don't understand why. The conditions (secondary halide and strong base) are already given in the problem. On earth, which conditions does the solution refer?
2. Ar-CH2C(C2H5)CH3Cl + Br- ---> ?A. Double bond formation
B. Loss of optical activity
The answer is B.
The problem gave tertiary halide and good nucleophile but weak base (Br-). According to the table in Kaplan lesson book p301, both E1 and Sn1 can occur. E1 means doulbe bond formation, and Sn 1 means loss of optical activity. So I think the answer can be both A and B. However, the solution said the answer is only B.
Can anybody explain the solution? Thank you~
