I\'m not sure about the second question. The S_N 2 reaction in Week 2 is perform

Question

I'm not sure about the second question. The S_N 2 reaction in Week 2 is performed with excess tert-butylamine in N-methyl-2-pyrrolidinone (NMP). In addition to bupropion, HBr is generated as a byproduct, which forms a salt with the excess tert-butylamine. Which of the following statements correctly describes why the salt is formed with tert-butylamine and not with bupropion? If all statements are correct, choose letter "D." A. The nitrogen in bupropion is part of an amide, so its lone pair is involved in resonance and thus isn't basic. B. The nitrogen in bupropion is less basic because it is near the carbonyl (C = 0), which reduces the basicity of the nitrogen by inductively withdrawing electron density from it. C. The nitrogen in bupropion is part of a chirality center, and nitrogens on chirality centers are not basic. D. All of the above. If methyl amine (MeNH_2) was used instead of tert-butylamine in the S_N 2 reaction, the rate would be: A. Faster B. Slower C. Unaffected

Explanation / Answer

Ans: B) The nitrogen in bupropion is less basic because it is near the carbonyl, which reduces the basicity or the nitrogen by inductively withdrawing electron density from it.

Ans: A) Faster: methyl amine is sterically less hindered so rate of SN2 will be fast.

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