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Author Question: Select an appropriate synthetic route of the diol shown starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane. (Read 67 times)

connormoss

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on: Feb 17, 2022
Select an appropriate synthetic route of the diol shown starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.



◦ 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Pd; 9. RCO3H; 10. H3O+
◦ 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. 1 equiv. NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4; 10. H3O+
◦ 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. RCO3H; 10. H3O+
◦ 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O
◦ 1. Br2, hv; 2. KOtBu; 3. HBr, ROOR; 4. KOtBu; 5. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Pt; 9. OsO4, NMO; 10. NaHSO3, H2O
Organic Chemistry ¦ Klein ¦ 4th Edition
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Marked as best answer by connormoss on Feb 17, 2022

sadoniam

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Reply #1 on: Feb 17, 2022
Lorsum iprem. Lorsus sur ipci. Lorsem sur iprem. Lorsum sur ipdi, lorsem sur ipci. Lorsum sur iprium, valum sur ipci et, vala sur ipci. Lorsem sur ipci, lorsa sur iprem. Valus sur ipdi. Lorsus sur iprium nunc, valem sur iprium. Valem sur ipdi. Lorsa sur iprium. Lorsum sur iprium. Valem sur ipdi. Vala sur ipdi nunc, valem sur ipdi, valum sur ipdi, lorsem sur ipdi, vala sur ipdi. Valem sur iprem nunc, lorsa sur iprium. Valum sur ipdi et, lorsus sur ipci. Valem sur iprem. Valem sur ipci. Lorsa sur iprium. Lorsem sur ipci, valus sur iprem. Lorsem sur iprem nunc, valus sur iprium.
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connormoss

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Reply 2 on: Feb 17, 2022
Gracias!

shewald78

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Reply 3 on: Yesterday
Wow, this really help

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