Homework 5a - are required to produce each of the following...

Info iconThis preview shows pages 1–3. Sign up to view the full content.

View Full Document Right Arrow Icon
Homework 5a Fall 2009 1. Write mechanism for the formation and structure of X which, in the presence of enzyme and NADH gives an aminoacid tryptophan. Write mechanism for the final product as well. Show structure of NADH/NAD+ H 2 O enzyme [X] H + + NH 3 N H O COO H N H NH 2 CO OH NA DH + 2. Show step by step mechanisms for the following transformations: OH H a. H + /H 2 O O H OH H HO - /H 2 O O H b. c. OH O enol H + /H 2 O d. OH O HO - /H 2 O TAUTOMERIZATIONS 3. Propose the mechanism for the following imine formation. Indicate where will be C-14 labeled carbon in the cyclic compound. H + N * - corresponds to 14 C NH 2 O *
Background image of page 1

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

View Full DocumentRight Arrow Icon
4. Propose a mechanism for the following transformation: NH 2 OH + H O O O H + O N H +3 EtOH 5. Propose mechanism for the following transformations: OH O H O OH OH OH H + /H 2 O H + /H 2 O α -hydroxyaldehyde ene-diol α -hydroxyketone 6. Write what reactants ( with less carbon atoms than the final product ), catalysts or reagents
Background image of page 2
Background image of page 3
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: are required to produce each of the following in one step . (where H + or HO-workup does not constitute a step) a. b. c. COOH d. OH O O 7. Using benzaldehyde as a starting material and reagents that provide no more than 1 carbon to the final product show synthesis of the following: CHO 8. Propose reasonable syntheses for the following: O OH O 9. Draw the structure of the product of each of the following reactions: CHO + P(C 6 H 5 ) 3 + O Ph 3 P=CHC 6 H 5 O + Ph 3 P=CH 2 10*. For the brave: Enamines are very useful intermediates that are used to alkylate ketones and aldehydes. Here is an example of the synthesis using enamine. Attempt reasonable mechanisms for all the steps: O N H O cat. H + N O Br N O H + /H 2 O O...
View Full Document

Page1 / 3

Homework 5a - are required to produce each of the following...

This preview shows document pages 1 - 3. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online