HW3Final_KEY - Sessler CH310M/318M Homework Problem Set 3...

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Sessler CH310M/318M Homework Problem Set 3 Due Wednesday Oct. 1 1 Please write the first three letters of your last name in the above boxes Name:____________ KEY ___________________ UT EID:_____________________________ Signature:____________________________
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Sessler CH310M/318M Homework Problem Set 3 Due Wednesday Oct. 1 2 (please include this page as page two in your homework set) Score:_________
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Sessler CH310M/318M Homework Problem Set 3 Due Wednesday Oct. 1 3 1. Please fill in all substituents including hydrogens on C 1 , C 2 , and C 3 on the alternative chair conformation shown on the right side of the equilibrium. Then, fill in the box with the appropriate equilibrium arrows (i.e. ) and in one sentence explain your choice. (a) Sentence: The chair conformation with the larger group, t -butyl, in equatorial position is more stable (- Δ G ° for axial to equatorial conversion is 21.0 kJ/mol for –C(CH 3 ) 3 and 7.28 kJ/mol for –CH 3 ). (b) Sentence: Both chair conformations have one methyl group equatorial and one axial, and are therefore equal in energy. (c) Sentence: The only difference between these two conformers is an -OH vs. -CH 3 in the equatorial or axial position making the conformer on the right more stable as the - Δ G ° for axial to equatorial conversion for –OH is only 3.9 kJ/mol as opposed to 7.28 kJ/mol for –CH 3 .
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This note was uploaded on 03/23/2010 for the course CH 54410 taught by Professor Sessler during the Spring '10 term at University of Texas at Austin.

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HW3Final_KEY - Sessler CH310M/318M Homework Problem Set 3...

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