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Unknown Compound A and B and their Reactions

Identify the unknown compound A and B and their reactions with H2 on a catalyst and acidic permanganate. Draw missing structures and mechanisms to explain the reactions.

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Unknown Compound A and B and their Reactions

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  1. Problem A symmetrical unknown compound A, C8H16, reacts with H2 on a 1% Pt/C catalyst to form B (C8H18). Treatment of A with acidic permanganate affords butanone only. Identify A and B.

  2. KMnO4, H3O+

  3. Draw the missing structures.

  4. Draw the structure of the main product(s) formed.

  5. Addition to Conjugated Dienes resonance forms of the allylic carbocation

  6. The 1,2-addition product is typical Markovnikov. The 1,4-addition product is due to the resonance forms of the allylic carbocation intermediate.

  7. Draw a mechanism to explain the following reaction: Hint: Why are there two products?

  8. The Hydride Shift

  9. Opportunistic Carbocations!

  10. a-Terpinene, C10H16 (A), is a pleasant-smelling hydrocarbon that has been isolated from oil of marjoram. On hydrogenation over a palladium catalyst, a-terpinene reacts with 2 equivalents of hydrogen to yield a new hydrocarbon, C10H20 (B). On reaction with acidic KMnO4, a -terpinene yields the compounds below. Propose a structures for A and B. Outline all chemical reactions.

  11. Alkynes Reaction Acidity Synthesis

  12. s-Complex of Acetylene p-Bonds

  13. Catalytic Hydrogenation

  14. Hyddrogenation with Lindlar’s Catalyst forms cis Alkenes

  15. H2 on a Poisoned CatalystPrevents Over-Reductioncis Alkenes

  16. Addition of HX

  17. Br2 Addition

  18. Oxymercuration HydrationMarkovnikov

  19. Enol – Keto TautomerizationIntermolecular

  20. Hydroboration HydrationAnti-Markovnikov

  21. Draw the Products

  22. Acidity of Terminal Alkynes

  23. Acetylide Formation

  24. Alkylation of Acetylide IonsReaction with alkyl halides

  25. Multi-step Syntheses

  26. Retrosynthetic AnalysisBegin with the Product

  27. Fill in the Reagents

  28. Outline the synthetic steps. Indicate all necessary reagents for each step.

  29. 5 Steps

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