(A) to (B) is simply reduction, tosylation followed by intramolecular reaction and removal of tosylate. However, I am not able to guess how dimerization will take place, seems similar to Rauhut–Currier reaction, but can't guess. Any hint?
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2$\begingroup$ TsOH does not form a tosylate. That's likely just the workup for the borohydride reduction. $\endgroup$– ZheMay 1, 2020 at 15:31
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1$\begingroup$ My hint for you is that you can determine the which of A through D is mostly likely to be the product (B) based on several factors. Then working backwards, you can figure out what (A) is. $\endgroup$– ZheMay 1, 2020 at 15:38
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1$\begingroup$ @Zhe Don't TsOH tosylate like TsCl? I didn't know that, if that's true. Thanks, any other way to get the answer? Any proposed mechanism? $\endgroup$– ZenixMay 1, 2020 at 16:41
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2$\begingroup$ That's kind of like how you can (sort of) alkylate stuff using alkyl chlorides RCl, but you can't alkylate stuff using alcohols ROH. $\endgroup$– orthocresolMay 1, 2020 at 16:58
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2$\begingroup$ No tosic acid is not like tosyl chloride, in the same way methyl alcohol is not like methyl chloride. I have a putative mechanism, but I thought I'd let you try to figure it out for yourself first. $\endgroup$– ZheMay 1, 2020 at 16:58
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1 Answer
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The dimer of methyl vinyl ketone (1) is not shown in the choices in the question. The dimer is A shown below. It is a "tail-to-tail" dimer. Product B is an intramolecular ketal as a probable mixture of epimers. Compare with this paper.
B. P. Mundy, et al., J. Org. Chem., 1978, 43, 2347.
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$\begingroup$ Don't have access to the paper... And I still can't get the mechanism for dimerization.... $\endgroup$– ZenixMay 1, 2020 at 17:41
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$\begingroup$ You can usually predict Diels-Alder reactions by using ionic charges. This one is probably radical in nature. Whoever made up the structure (B) fell into this trap. $\endgroup$ May 1, 2020 at 17:45