Question

Predict the major organic products formed in the following reactions. Be certain to indicate stereochemistry in your products if it is important. H2 Pd/C HCI H2O H2SO4 Br2 Draw a stepwise, detailed mechanism for the acid-catalyzed hydration reaction in question 2 above. Use curved arrows to indicate the flow of electrons. (Note: use hydronium ion, H307, in your mechanism to indicate “acidic water”).

Answer 1

CH3 111111 Syn-addition of Parc сн» hydrogen to the Catalytic double bond hydrogenation HCl . more stable 30 carbocation (major) less stable not formed Trans-fusion Trans more major fusion stable Cis-fusion minor less stable 4 HH More - severe trans-axial repulsion This is why cis-fused decalin is less stable . BT Brzy De ..CH₂ CH₂ Br

* sana Bye or Br , POCHCH₂o as Ô CHCH с ,сня La CH2 CH3 less stable more stable 30 - carbocation - 20 carbocation This carbon can stabilize partial negative charge the ราค3+ Bro is atto pacted to attack this carbon instead of the less hindered one. Note: This rationalization holds good for any strained & charged intermediate like this one. (3-membered sing 3. ve her son vKOH (Product) Mechanism ole tok H2O. Kot eneo his Ho® » А , ,4 - l [+H*7 more stable L+H . Bo carbocation is formed wton addition of Ht [+H7 so Note: Acid, is seid, ie. Ht is catalyst, so addition i elimination, EHIJ in the last d of u stet and

Note: wherever two products are written, under it 'major' is written for the product.