НООС OH 1 2 H2 1. p-Toluenesulfonic acid Oppenauer Oxidation HO Lindlar Catalyst 2. H2, Pd/C

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Complete the synthesis reaction showing curved arrows and mechanisms for each reaction. 

НООС
HO
2.
H2
1. p-Toluenesulfonic acid
Oppenauer
Lindlar Catalyst
2. Н2, Pа/c
Oxidation
HO
Transcribed Image Text:НООС HO 2. H2 1. p-Toluenesulfonic acid Oppenauer Lindlar Catalyst 2. Н2, Pа/c Oxidation HO
Expert Solution
Step 1

For the above organic synthesis, the following transformations must be known:

1. Hin presence of Lindlar's catalyst reduces alkyne to cis-alkene.

2. p-Toluenesulfonic acid reacts with 3o alcohol to form tosylate and elimination occurs.

3. H, Pd/C reduces alkenes to alkanes.

4. Oppenauer Oxidation is a simple method for selectively oxidizing 2o acohols to ketones. 

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