SS13 E3 - Practice exam PDF

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CHE 321 Summer 2013

Exam 3

Form 1

Multiple Choice Questions: 50 points 1. Below shows different reactions of 3-methyl-1-butene. Select the reaction that shows the incorrect major product.

2. Choose the best synthetic route for making 3-bromohexane from bromoethane.

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CHE 321 Summer 2013

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3. Choose the order that has the following reagents correctly arranged with respect to increasing elimination product (vs. substitution) upon reaction with 1-bromobutane.

4. Select the major product of the following reaction sequence.

5. Select the order that has the following hexenes correctly arranged with respect to increasing 3-hexanol product when subjected to hydroboration/oxidation.

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CHE 321 Summer 2013

Exam 3

Form 1

6. Select the best reaction conditions to convert compound A into 3-methyl-2-hexanol, based on the following information given below.

7. Choose the major product of the following reaction.

8. Choose the major product from the following reaction involving a deuterium-labeled borane.

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CHE 321 Summer 2013

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9. Select the major product from the following reaction sequence.

10. Choose the alkene that, upon reaction with bromine in water, would give the following racemic mixture as the major product.

Short Answer Questions: 50 points 11. Draw the structure(s) of the major product(s) of the following reaction. 5 pts

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CHE 321 Summer 2013

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12. Draw the structure(s) of the major product(s) of the following reaction. 5 pts

13. Draw the structure of the major product(s) of the following reaction. 5 pts

14. There are four alkenes with the molecular formula C6H10 that upon hydrogenation give methylcyclopentane. Out of those four alkenes, only one gives a meso product upon reaction with osmium tetroxide. Draw the structure of that alkene. 5 pts

15. Compound A has a molecular formula of C6H12. Compound A reacts with H-Cl to give one major product, B, which is achiral. If you bubble in choice A next to number 18 on your scantron, you will receive 5 bonus points towards your overall course total. When compound A is treated with ozone, followed by dimethyl sulfide, a single product is obtained with molecular formula C3H6O. Clearly draw the structures of compounds A and B. 10 pts

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CHE 321 Summer 2013

Exam 3

Form 1

16. Using the curved arrow formalism, show all the bond making and bond breaking steps of the following reaction. HINT: the initial carbocation will rearrange to form a more stable carbocation. 10 pts

17. Propose a synthesis of the following compound starting from any compound(s) containing four carbon atoms or less. 10 pts

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