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(11 ) Greg Nard added an equivalent of3,4-epoxy-4-methylcyclohexanol (Figure 1)

ID: 691048 • Letter: #

Question

(11) Greg Nard added an equivalent of3,4-epoxy-4-methylcyclohexanol (Figure 1) to an ether solution ofmethyl magnesium bromide and then added dilute hydrochloric acid.He expected that the product would be a diol (Figure 2). He did notget any of the expected product. What product did he get? Fig. 1 Click image to launch MarvinView™
Fig. 2 Click image to launch MarvinView™ (11) Greg Nard added an equivalent of3,4 - epoxy - 4 - methylcyclohexanol (Figure 1) to an ether solution ofmethyl magnesium bromide and then added dilute hydrochloric acid.He expected that the product would be a diol (Figure 2). He did notget any of the expected product. What product did he get?

Explanation / Answer

Grignard reagent MeMgBr will react with the OH group ofcyclohexanol give methane and CH3(Oepoxy)C6H3OMgBr.