enter image description here I was asked to find the products X and Y. For the product X,Here the grignard reagent and even the carbonyl substrate was too sterically hindered to approach the carbonyl center so no reaction would take place, thus the final product will beenter image description here

I thought the same for Y product .. Here the Carbonyl compound was crowded to approach so no reaction would take place but then I found the answer to be this. enter image description here

So for the product Y hydrolysis occured due to presence of dilute HCl but it did not occur for the first one. But why? And was I right about the logic above?

  • 1
    $\begingroup$ organic-chemistry.org/namedreactions/grignard-reaction.shtm Scroll a bit down. The grignard reagent used for [Y] is most likely to bulky to deprotonate the $\alpha$ hydrogen. $\endgroup$ – Avyansh Katiyar Jan 23 '19 at 15:29
  • $\begingroup$ @Soumik Das take a look at the reference Avnish Kabaj linked to. Reduction can occur when there is too much hindrance for nucleophilic attack $\endgroup$ – Waylander Jan 23 '19 at 16:21
  • $\begingroup$ @Waylander Hmm. Pretty unusual though. $\endgroup$ – Soumik Das Jan 23 '19 at 16:24
  • $\begingroup$ @AvnishKabaj That means we will get three products in total; and the reduced one is given as a side product though.. That means the product by SET mechanism will be major, isn't it? $\endgroup$ – Sarah jane Jan 23 '19 at 16:35
  • 1
    $\begingroup$ i.stack.imgur.com/Q2G6A.png Looks like the major product will be the reduced form and minor will be the enolized form and surprisingly zero percent addition product. $\endgroup$ – Avyansh Katiyar Jan 23 '19 at 17:03

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Browse other questions tagged or ask your own question.