Conant J. B.'s The Study of Absorption Spectra of Organic Compounds at PDF

By Conant J. B.

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Extra info for The Study of Absorption Spectra of Organic Compounds at Liquid Air Temperatures

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Identify these atoms and draw a mechanism and products for each reaction. H N H Ph Ph Me Me Ph P OH O Purpose of the problem Considering possible alternative reactions. One of the reactions might seem trivial, but it isn’t. Suggested solution In each case one of the electrophilic sites is an acidic proton. There is also the electrophilic π bond (C=N+ or C=O). For the first case, we draw the two reactions separately. 37 Solutions for Chapter 5 – Organic reactions H N Me H H Me Me H N Nu H Me H H N Nu Me Me Me N Me Nu In case you were seduced by the positively charged nitrogen atom (we hope you weren’t), we should also remind you of a reaction that most definitely cannot happen: direct attack at N: the supposed product has an impossible five bonds to nitrogen.

OH OH + O O H + H OH + O O OH HO O OH OH O O H O HO PROB LE M 8 Trichloroethanol my be prepared by the direct reduction of chloral hydrate in water with sodium borohydride. Suggest a mechanism for this reaction. Take note that sodium borohydride does not displace hydroxide from carbon atoms! HO OH H Cl3C × NaBH4 H2O chloral hydrate OH Cl3C trichloroethanol H HO OH H H Cl3C H B H this is not the mechanism Purpose of the problem To help you detect bad mechanisms and find concealed good ones. Suggested solution If sodium borohydride doesn’t displace hydroxide from carbon atoms, then what does it do?

Which ketone is hydrated and why? O O O Purpose of the problem To let you think practically about reactions that may give more than one product. Suggested solution The two ketones next to the benzene ring are stabilized by conjugation with it but also destabilized by the central ketone—two electron-withdrawing groups next to each other is a bad thing. The central carbonyl group is not stabilized by conjugation and is destabilized by two other ketones so it forms the hydrate. Did you remember that hydrate formation is thermodynamically controlled?

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The Study of Absorption Spectra of Organic Compounds at Liquid Air Temperatures by Conant J. B.

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