Dr.

Manashi Chatterjee Week-2-Recitation Chem 224

1. Give the major product of the following reactions. Please indicate stereochemistry
where ever possible. Clearly indicate if a racemic mixture is formed. If no reaction
occurs write the starting material that is being used for that step.

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Dr. Manashi Chatterjee Week-2-Recitation Chem 224

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Dr. Manashi Chatterjee Week-2-Recitation Chem 224

1. Give the major product of the following reactions. Please indicate stereochemistry
where ever possible. Clearly indicate if a racemic mixture is formed. If no reaction
occurs write the starting material that is being used for that step.

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Dr. Manashi Chatterjee Week-2-Recitation Chem 224

2. Provide the reagents in correct order to achieve the following transformation.

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Dr. Manashi Chatterjee Week-2-Recitation Chem 224

3. Show how you would synthesize 3-methyl-4-hexyn-3-ol starting with acetylene and
any necessary additional reagents. Show products from each step.

4. A compound with MF: C13H22 on ozonolysis (O3 followed by Me2S) gave the
following carbonyl compounds. Propose the structure of the starting compound.

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Dr. Manashi Chatterjee Week-2-Recitation Chem 224

5. Using curved arrows show detailed mechanism for reaction of lactones with excess of
phenyl magnesium bromide.

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Dr. Manashi Chatterjee Week-2-Recitation Chem 224

6. Using curved arrows show detailed mechanism for dehydration of Diol X to form
Ketone Y?