This site requires Javascript to be turned on. Please enable Javascript and reload the page.

Organic Chemistry

SOLUTION 12.3c

STEP 1: Hydrogenation with H₂ on Pt would not stop at the alkene… need Lindlar’s catalyst or Ni₂B to make a cis-double bond by hydrogenation of an alkyne.

STEP 2: Although this product is not technically incorrect, it is incomplete. You do make the “syn” diol, but the oxygens could add from the top or bottom face of the alkene so you would make a racemic mixture, not an enantiomerically pure product.

This page is referenced by:

Lectures 12 and 13: Alkenes II & III 8 image_header 2020-03-14T14:55:54-07:00
Objectives and Skills

KEY INFORATION SUMMARY
PROBLEMS

Problem 12.1: Mechanisms
1. Add the curved arrows to complete each transformation below (extra intermediates may need to be drawn). How many stereoisomers of the major product would be formed for each reaction? SOLUTION
b. How many stereoisomers of the major product would be formed for each reaction? SOLUTION

If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move the problem below ;)

Problem 12.2: Reaction Coordinate Diagrams
1. Draw a mechanism and reaction coordinate diagram to describe the reaction below. SOLUTION
2. Explain why the major product is favoured. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move the problem below ;)

Problem 12.3: Reactivity
1. Fill in the missing pieces to complete the transformations below. SOLUTION
1. Predict the products for the multi-step synthesis below. SOLUTION
1. Find the error in the two-step synthesis below. Propose a corrected synthesis. SOLUTION
1. The following compounds were obtained after the ozonolysis (1. O₃, 2. H₂S) of an unknown alkene. Identify the structure of the alkene. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move the next lecture ;)

This page is referenced by:

This page references: