Final_M10 - CHEM 109A Russak M 10 Final Question 1 ______/2...

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Unformatted text preview: CHEM 109A Russak M 10 Final Question 1 ______/2 Question 2 ______/9 Question 3 ______/6 Question 4 ______/24 Question 5 ______/6 Question 6 ______/4 Question 7 ______/6 Question 8 ______/9 Question 9 ______/8 Question 10 ______/12 Question 11 ______/15 Total ______/100 Name____________________ Perm #___________ 1. Circle the alkyl halide that undergoes the slowest SN2 reaction: (2) 2. Give the product(s) of the following substitution reactions to include stereochemistry. (9) 3. a. In the substitution reaction of methyl bromide with hydroxide ion, the rate of the reaction is accelerated upon the use of DMSO as a solvent as opposed to ethanol. Explain why. (3) b. In an SN2 reaction, what effect would doubling the concentration of the nucleophile have on the rate of the reaction? What about an SN1? Use rate expressions to support your claim. (3) 4. a. Predict the substitution products. You don’t need to show stereochem (12) b. Give the following elimination products. You don’t need to show stereochem. (12) 5. Consider the following structure under E2 conditions. Are there E2 products? If so, draw them. If not, illustrate and explain why. (6) 6. Consider the effect that the solvent plays in an SN1 type reaction: (4) a. For a charged reactant: b. For a neutral reactant: 7. Predict the product of the following reaction. Also, if the halohydrin below were 1 carbon less, would this be more or less advantageous in an intramolecular reaction. Explain. (6) 8. Predict the product of the following reactions based on the structure of the reactants, the base, solvent, etc…. State whether or not it is E1, E2, SN1 or SN2. (9) 9. Draw a possible mechanism for the following transformation: (8) 10. Predict the product of the following sequences of reactions or predict the starting materials based on the product: (12) 1. BH3/THF 2. NaOH, H2O2, H2O 3. PCC 1. Hg(OAc)2, THF/H2O 2. NaBH4 3. H2CrO4 CH3 ! O OM e O 11. Propose a synthesis from the reactant to the product. (15) Cl CN CN ...
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This note was uploaded on 09/09/2011 for the course CHEM 109A taught by Professor Bruice during the Spring '07 term at UCSB.

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