Week 1 - gsw orgo 2 worksheet questions PDF

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gsw orgo 2 worksheet questions...

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GSW Problem Set #1 Organic Chemistry 210-2 for Winter 2014

1. Provide a mechanism for the following reactions. Include all proton transfer steps. Show movement of electron pairs with arrows. Show resonance structures for intermediates in brackets. a.

OH

catalytic H2SO4 O

O

O

b. O O H2SO4 catalytic

2. Suggest a sequence of reactions for carrying out the conversions shown below. In addition to cyclohexene, you may use any necessary inorganic reagents and alcohols having four or fewer carbons. Draw the structures of each intermediate products that you would need to isolate in your synthesis and indicate the necessary reagents for each step. If you change your mind, you must erase or cross out the parts of your answer that you do not want to have graded. You need not show reaction mechanisms. a. OH

b. OH

c. O

3. Draw a curved arrow mechanism for the following reactions. a) O

OH

H+, H2O

H

HO O

b) O

H H+, H2O

H2C C C

c) (STN_Wi99_MT2-3). O

HgSO4 in H2SO4 HO

OH O

4. Draw the major product or products expected from the following reactions and the mechanisms for their formation. Clearly show the product stereochemistry in part a. a. H3C H Cl

OH H CH3

b. + HBr

t-BuO-K+ - HCl

5. Suggest a sequence of reactions for carrying out the conversions shown below. In addition to cyclohexene, you may use any necessary inorganic reagents and alcohols having four or fewer carbons. Draw the structures of each intermediate products that you would need to isolate in your synthesis and indicate the necessary reagents for each step. a. OH

b. O O CH3...