Chemistry

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):

______ of 10 points

PROBLEM 2. Give the reagents for the following reactions:

______ of 10 point

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

______ of 10 point

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

Structure Name

1-ethoxybutane (butyl ethyl ether)

pentane-2,4-diol

8,8,8-trichloro-3-ethyl-7-methyloctan-2-ol

2-mercaptoethanol

Pyridine

_____of 10 points

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).

_____of 10 points

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:

_____of 10 points

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.

_____of 10 points

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

_____of 10 points

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:

______ of 10 points

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

A

B

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