chm2210ps23sol

chm2210ps23sol - light Locate C-14 in product CH 2 CH CH 2...

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C O CH 3 Organic Chemistry I Problem Set 23 Answer Key Conjugated Dienes I. Write structural formulas for important products. 1. 2. 3. 4. 5. 6. 1 mol Br 2 CH 2 =CH-CH=CH 2 1 mol HCl Cl 2 h NBS 2 mols NaOEt alcohol, heat CH 2 =CH-CHO excess H 2 Pt PBr 3 a. Li b. CuBr c. phenyl iodide CH 2 =CH-CH=CH 2 CH C C CH 3 O C CH H 2 C N excess H 2 Pt CH 2 CH CH 2 CH CH 3 Br K O-t-Bu heat Br Br Br Br + CH 2 CH CH CH 3 Cl CH 2 CH CH CH 3 Cl + Cl Cl Br CHO CH 2 OH CH 2 Br CH 2 CN CH 2 -NH 2 CH 2 =CH-CH 2 -CH=CH 3
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O O O 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. CH 3 -CH=CH 2 Cl 2 400° CH 3 -CH=*CH 2 NBS light 14 C Where is the C- 14 in the product? Cl 2 400° CH 3 CH 2 =CH-CH=CH 2 1 mol HBr 45° C (major) CH 2 =CH-CH=CH 2 1 mol HBr -15° C (major) CH CH H 2 C O + C CH CH C O O O CH 2 =CH-CH=CH 2 O O H H H H + C HC Cl * NBS
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Unformatted text preview: light Locate C-14 in product CH 2 CH CH 2 Cl + CH 2 CH CH 3 Cl Cl major Cl * * Cl + CH 2-Cl CH 3 Cl CH 3 Cl + + major * Br * Br * Br * Br + + + CH 3-CHCl-CH=CH 3 CH 3-CH=CH-CH 2 Cl CHO CHO CHO Cl 18. 19. butane 1 mol Br 2 light KOtBu heat NBS light KOtBu heat CHO C CH a. O 3 b. Zn/H 2 O ethylene Br 2 CCl 4 1 mol KCN NaOCH 3 heat excess H 2 Pt 50C, 25atm CH 3 CH CH 2 CH 3 Br CH 2 CH CH 2 CH 3 CH 2 CH CH CH 3 Br CH 2 CH CH H 2 C CHO CHO CHO CHO Br-CH 2-CH 2-Br Br-CH 2-CH 2-CN CH 2 =CH-CN CN CH 2-NH 2...
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chm2210ps23sol - light Locate C-14 in product CH 2 CH CH 2...

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