SynthesisAnswer - 2 CH 3 NaNH 2 C C CH 2 CH 2 CH 3 CH 3 CH...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Name ________________________ Page 9 V. (30 points) Using ONLY the reagents listed on the side, design your own synthesis of the racemic mixture of diols shown below: H 2 (gas) Pd/BaSO 4 quinoline NOTE: mechanistic steps (curved arrows) should n o t be shown. Simply provide the reactants and products of the reactions needed to accomplish this synthesis. You will be graded on conceptual correctness as well as the validity of the reactions you choose. Be sure to show stereochemistry when appropriate. KMnO 4 H C C H H 3 C C C CH 2 CH 3 H C C H H H CH 3 CH 2 CH 2 Br CH 3 CH 2 CH 2 CH 2 CH 2 Br CH 3 CH 2 CH 2 CH 2 Br CH 3 CH 2 Br CH 3 Br H 3 CH 2 CH 2 C C C HO CH 2 CH 3 OH H H H 3 CH 2 CH 2 C C C H OH CH 2 CH 3 HO H H 3 O + C O O O H Cl Reagent Shelf 30 Br 2 BH 3 NaOH HBr NaNH 2 H 2 O 2 H 2 O Pt H C C H NaNH 2 (1 equiv) H C C CH 3 CH 2 CH 2 Br H C C CH 2 CH
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 2 CH 3 NaNH 2 C C CH 2 CH 2 CH 3 CH 3 CH 2 Br C C CH 2 CH 2 CH 3 H 3 CH 2 C H 3 CH 2 CH 2 C C C H OH CH 2 CH 3 HO H How do OHs add? Syn, so rotate to see how the Hs must have been added H 3 CH 2 CH 2 C C C H CH 2 CH 3 OH HO H S S S S when you remove the OHs, you can see that the double bond must have been E See Newman Above! H 3 CH 2 CH 2 C C C H CH 2 CH 3 H SO, picking up from above. ... C C CH 2 CH 2 CH 3 H 3 CH 2 C Na NH 3 Na NH 3 Pr H OH H Et HO HO Pr H H Et HO C C CH 2 CH 2 CH 3 H 3 CH 2 C H H KMnO 4 H 3 CH 2 CH 2 C C C H OH CH 2 CH 3 HO H + enantiomer...
View Full Document

Ask a homework question - tutors are online