Select an appropriate synthetic route to yield the given diol ...

[Maddie9229]

Question 1

Which of the reactions shown effectively produces 4,4-dimethyl-2-pentyne?



◦ I, III, and IV
◦ I, II, and IV
◦ I, II, and III
◦ I, II, III, and IV
◦ II, III, and IV

Question 2

Select an appropriate synthetic route to yield the given diol 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, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O
◦ 1. Br2, hv; 2. HBr, ROOR; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. NaHSO3, H2O
◦ 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. HBr; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Br; 8. H2, Lindlar’s catalyst; 9. OsO4, NMO; 10. NaHSO3, H2O
◦ 1. Br2, hv 2. HBr, ROOR; 3. KOtBu; 4. Br2; 6. xs NaNH2; 7. CH3Cl; 8. H2, Pd; 9. OsO4, NMO; 10. H3O+

[spicyzack]

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[Maddie9229]

Thanks for the timely response, appreciate it

[vickybb89]

YES! Correct, THANKS for helping me on my review