{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

Q6A-2005 - E and F(10 points 10 point bonus CO 2 Me Ph H 2...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
Chem 41c Quiz 6 Stoltz, Spring 2005 May 27, 2005 Predict the major products (if any) of the following reactions: (5 points each) 1. HNO 3 , H 2 SO 4 NO 2 2. H N HNO 3 , Ac 2 O, 20 °C H N NO 2 3. A remarkable cascade of pericyclic reactions on compound B produces a mixture of racemic compounds C - F simply upon heating. Compound B is prepared by Lindlar reduction of A . In a related system compound G is reduced to H and forms products I and J after prolonged stirring at 23 °C (eventually only J is observed). Your task is the following 1) identify the structures of B and H , 2) Describe a mechanism for the the conversion of H to I and J , (hint: it may be useful to draw an orbital diagram for H although not neccessary) and 3) As a bonus provide the mechanism for the formation of
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: E and F . (10 points, 10 point bonus) CO 2 Me Ph H 2 , Lindlar Catalyst CH 2 Cl 2 , 23 °C A B Ph CO 2 Me PhCH 3 , 23 → 100 °C H H H Ph H H H H MeO 2 C H H H Ph H CO 2 Me Ph H MeO 2 C H H Ph C D F E C and D are formed at 23 °C after prolonged stirring E and F are formed at 100 °C stirring during which time the amounts of C and D are diminished Intramolecular 4 + 2 Diels-Alder Cycloadditions CO 2 Me H 2 , Lindlar Catalyst CH 2 Cl 2 , 23 °C G H Ph PhCH 3 , 23 °C I J Ph Ph Ph Ph H Ph H Ph Ph 8 π conrotatory electrocyclization 6 disrotatory...
View Full Document

{[ snackBarMessage ]}