Dolbier HW Solutions 696

Dolbier HW Solutions 696 - 790 APPENDIX A A-9. Dissociation...

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A-9. Dissociation to give a secondary carbocation Rearrangement by hydride migration to give a tertiary carbocation Capture of the carbocation by water to give product B-1. ( b ) B-2. ( c ) B-3. ( d ) B-4. ( c ) B-5. ( d ) B-6. ( a ) B-7. ( c ) B-8. ( d ) B-9. ( c ) B-10. ( a ) B-11. ( a ) B-12. ( c ) B-13. ( c ) B-14. ( c ) CHAPTER 9 A-1. ( a ) 4,5-Dimethyl-2-hexyne ( c ) 6,6-Dimethylcyclodecyne ( b ) 4-Ethyl-3-propyl-1-heptyne A-2. ( a )( e ) ( b f ) Na, NH 3 ( l ) ( c )H 2 O, H 2 SO 4 , HgSO 4 ( g ) ( d h ) A-3. Reaction (2) is effective; the desired product is formed by an S N 2 reaction. Reaction (1) is not effective, owing to E2 elimination from the secondary bromide. 11 1 NaBr CH 3 C CNa CH 3 CH 2 CHCH
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