PROBLEM 1. Reactivity of Alcohols and Ethers. Give the structure of products for the following reactions (indicate major / minor where applicable) and show stereochemistry (where applicable):

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PROBLEM 2. Give the reagents for the following reactions:

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PROBLEM 3. Give the best starting material including stereochemistry that would provide the correct product with the stereochemistry shown:

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PROBLEM 4. Names of compounds/draw compounds from name.

Structure Name

1-ethoxybutane (butyl ethyl ether)





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PROBLEM 5. Rank the following in the order of a. ease of carbocation formation (like for E1 elimination) (1 = easiest elimination).

b. acidity of protons indicated (1 = most acidic).

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PROBLEM 6. Reaction Mechanism 1. Reaction of 3-methyl-2-butanol with HBr yields two products. One is the regular product of SN1 (2-bromo-3-methylbutaneminor product) and second (major) is the product of rearrangement. Write mechanism for the formation of this major product.

Draw the transition state for the rearrangement step:

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PROBLEM 7. Reaction Mechanism 2. Draw product and mechanism for the following reaction. Use curved arrow notation to indicate electron flow. Don’t need the mechanism for the workup step. Hint: Be mindful of the stereochemistry in the product.

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PROBLEM 8. Reaction Mechanism 3. Propose a detailed reaction mechanism to account for the following reaction. Use curved arrow notation to indicate electron flow.

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PROBLEM 9. Spectral Analysis. From the sets of molecules provided circle the molecule that will: a. best fit the following 1H NMR:

b. best fit the following 13C NMR:

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PROBLEM 10. Nuclear Magnetic Resonance. Predict the 1H NMR spectra for the following compounds. Include chemical shift, integration, multiplicity and intensity of the lines within a multiplet. No need to try estimating the Js. Give proper drawings for full credit.

______ of 10 points



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