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2

According to Bordwell $\mathrm{p}K_\mathrm{a}$ Table, $\mathrm{p}K_\mathrm{a}$ of $\ce{PhCH2COSPh}$ is $16.9$, which is compatible with alcoholic $\ce{OH}$. We all know that Grignard reagents and organolithium reagents are very susceptible to acidic hydrogens because they are strongly basic as well as nucleophilic. Between $\ce{t-BuLi}$ and $\ce{n-BuLi}$, $\...


2

One easy way is to do the first step as you have drawn making benzyl chloride, then treat that with KCN (in DMSO or use water/CH2Cl2 with a phase transfer catalyst) to give 2-phenyl acetonitrile then hydrolyse that with aqueous sulfuric acid as described in this Organic Syntheses procedure here To convert benzene to 2-phenylethanoic acid: benzene reacts ...


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Further to my comments above, I am going to offer my opinion that the book is wrong and the epoxide is not opened by sodium hydride as depicted. I have failed to find any literature examples of such a reaction and, in 40+ years as a synthetic chemist, I can recall no reactions in which $\ce{NaH}$, unmodified by other reagents, acts as a source of ...


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