Talk:2,2-Dimethoxypropane

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Reaction mechanism[edit]

Comment moved from Talk:2,2-Dimethoxypropane/Comments. Astronaut (talk) 03:34, 26 October 2009 (UTC)

The reaction mechanism presented for this article is incorrect and indicative of a lack of understanding of fundamental organic chemistry. Written correctly the figure would show that ketal formation proceeds via an oxocarbenium type intermediate which is subject to nucleophilic attack at a formally sp2 hybridized center. The mechanism accompanying the article presently invokes SN2 type reactivity at sterically hindered sp3 hybridized carbon centers, which is not reasonable. Furthermore the dicationic structure presented is relatively high in energy and not appropriate since a mechanism commensurate with experimental data may be written with only neutral and monocationic species which are lower in energy. Having taught several semesters of undergraduate organic chemistry at Cal, I can say firmly that if this were a quiz or an (easy) exam question it would not receive full credit, in fact I would give it zero points in such a scenario. If I had chemdraw on my PC, I'd replace the figure immediately. — Preceding unsigned comment added by 67.188.13.101 (talk) 22:12, 24 October 2009

I agree that the reaction mechanism is inaccurate, so I have removed it. -- Ed (Edgar181) 11:52, 26 October 2009 (UTC)

Formation of peroxides[edit]

Does 2,2-DMP form peroxides on prolonged exposure to air? This is listed in a few MSDS records, though was removed from the piece Nick Semenkovich (semenko) (talk) 02:11, 6 September 2013 (UTC)