0
$\begingroup$

I know that a grignard reagent will formed will be formed but if you look at his question then the answer of this question is b. so I just want to know if something like wurtz reaction will take place if there is some another explanation for this answer.enter image description here

$\endgroup$
2
  • $\begingroup$ Consider that many Grignard reagents are commercially available including cyclohexyl magnesium bromide, and thus are stable in solution for months if not years. $\endgroup$
    – Waylander
    Commented Feb 10, 2020 at 8:35
  • $\begingroup$ The mix of products would depende very strongly on how the reaction was conducted and how it was worked up. And on the exact amount of magnesium used. I'd say, without that detail, it is a bad question. $\endgroup$
    – matt_black
    Commented Feb 11, 2020 at 15:43

1 Answer 1

1
$\begingroup$

In 1930, Palmer and Kipping1 reported the formation of cyclohexyl magnesium bromide in ether in 50-60% yield. They did not make an effort to detect the coupling product, "bicyclohexyl" [choice (b)] in the Grignard reagent itself. Subsequent reaction of the Grignard reagent with SiCl4 led to the isolation of bicyclohexyl and some cyclohexene. Although the authors did not speculate on the source of these products, it is likely that they are part of the 40-50% of the "missing" Grignard reagent formed by Wurtz-like coupling and elimination, respectively.

enter image description here

The following year, Gilman and Zoeller2 reported their results on the relative merits of forming cyclohexyl magnesium bromide and chloride. Cyclohexyl chloride gave generally higher yields than the corresponding bromide, and under their conditions, higher yields than what Palmer and Kipping had obtained.

enter image description here

To answer your question, it appears that both bicyclohexyl and cyclohexene may be by-products during the formation of cyclohexyl Grignard reagents.

1) K. W. Palmer and F. C. Kipping, J. Chem. Soc., 1930, 1020.
2) H. Gilman and E. A. Zoellner, J. Am. Chem. Soc., 53, 1931, 1945.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge you have read our privacy policy.

Not the answer you're looking for? Browse other questions tagged or ask your own question.