chm2210ps22sol

chm2210ps22sol - 1. N.R. 2. 3. 4. 5. 6. 7. 8. 9. 10. CH 3 C...

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Organic Chemistry I Problem Set 22 Answer Key Alkynes I. Show the steps you might use in carrying out these conversions: Use any other reagents, but make sure to use the carbon’s in the original compound in the product. 1. 2-propanol to cis -2-butene 2. 1-butene to 2-butyne 3. 2-chlorobutane to trans -1,2-dimethylcyclopropane CH CH 3 CH 3 OH H 3 PO 4 heat CH 2 CH CH 3 Br 2 CH 2 CH CH 3 Br Br 2mols NaNH 2 heat CH C CH 3 CH 3 Br CH 3 C C CH 3 Lindlar's H 2 H CH 3 CH 3 H Br 2 CH CH CH 3 Br Br CH 3 2mols NaNH 2 heat CH 3 C C CH 3 CH 3 CH 3 H H CH 3 CH CH CH 3 CH 3 CH CH 2 CH 3 Cl Li / NH 3 CH 2 I 2 Zn(Cu) CH 3 H H CH 3 CH 2 CH CH 2 CH 3 HBr CH 3 CH CH 2 CH 3 Br KOH EtOH CH 3 CH CH CH 3 Br 2 CH 3 CH CH CH 3 Br Br 2 mols NaNH 2 heat CH 3 C C CH 3
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4. 2-butanol to butanone 5. cyclohexanol to adipic acid H 3 PO 4 heat Br 2 CH CH CH 3 Br Br CH 3 2mols NaNH 2 heat CH 3 C C CH 3 CH 3 CH CH CH 3 CH 3 CH CH 2 CH 3 OH Hg +2 / H 2 SO 4 reflux CH 3 C CH 2 CH 3 O OH H 3 PO 4 heat KMnO 4 H 3 O + , heat O O HO OH
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II. Write structural products for the reactions below. If no reaction write N.R.
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Unformatted text preview: 1. N.R. 2. 3. 4. 5. 6. 7. 8. 9. 10. CH 3 C C CH 3 + NaNH 2 + NaNH 2 CH C CH 3 CH 3 C C CH 3 H 2 / Ni 2 B + NaNH 2 CH C CH 3 CH 3 CH 2 CH 2 Br C CH NaNH 2 CH 3 Br H 2 excess Pt CH 2 CH CH 3 Br 2 2mol NaNH 2 heat H 2 excess Pt cis-1,3-pentadiene CH 3 CH CH 2 CH 3 OH H 2 SO 4 heat CH 3 CH CH 2 CH 3 Br NaOEt heat CH 3 CH CH 2 CH 3 Br K O-t-Bu heat C C CH 3 + NH 3 + Na CH 3 CH 2 CH 2 CH 3 H 3 C C C CH 2 CH 2 CH 3 CH 2 CH 2 CH 3 CH C CH 3 CH 3 CH 2 CH 2 CH 2 CH 3 CH 3 CH CH CH 3 CH 3 CH CH CH 3 CH 2 CH CH 2 CH 3...
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This note was uploaded on 02/23/2010 for the course CHEM 201 taught by Professor Smith during the Spring '10 term at Duke.

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chm2210ps22sol - 1. N.R. 2. 3. 4. 5. 6. 7. 8. 9. 10. CH 3 C...

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