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Chemistry 251/253 |
Homework 6 Answer Key |
1. 
CCOC(=O)C1(Cc2ccccc2)CCCCC1=O
2.
CCC1CCC(C)C1=O
3.
CC(=O)C(=C1CCC2CCCCC2C1)C(=O)C
4.
5.
CCOC(=O)C(CC(C)C(=O)C)C#N
6. Each of the following compounds may be prepared by a crossed-Claisen condensation. However, you should expect the yield of one of the compounds to be much less than the other three. Enter the letter corresponding to this compound in the appropriate text field.
7. Select the structure that did not result from the condensation
of two esters:
8.
CCCC1(C)SCCCS1
9. Draw the structure of compound A in the following reaction sequence:
CC(C=O)c1ccccc1
10. What is the hybridization of the oxygen atom in
? sp2
11.
CCOC(=O)CC(=O)c1ccccc1
12.
CCOC(=O)C(C(=O)OCC)c1ccccc1
13.
C=C(C1CCC[N]1)c2ccccc2
14. 
O=C1CCCCC1CN2CCCC2
15.
CC(=O)C1C2CCCC(=O)C2CCC1=O
16.
CCOC(=O)CC(=O)CC
17. Draw a chemically reasonable structure for the intermediate involved in this biosynthetic transformation.
C[N+]1=CCCC1
18. Only one of the following reactions will proceed as indicated. Which one?
19. Draw the structure of compound B. CCN(CC)C(=CC)CC
20. Draw the structure of compound D. CCC(=O)C(C)C1(C)CCCC(=O)C1
21. When Polly Ester ran the following reaction-
, she obtained two products, both of which had the same
elemental analysis: C 63.5% H 8.3% O 28.2% . Draw the structure of
the major product.
CCOC(=O)C1(C)CCCC1=O
22.
CCC1C(=O)N(C)C(=O)N(C)C1=O
23.* Draw the enol intermediate in the following decarboxylation:
C/C=C(\C)/O
24. Draw the structure of compound F. N#CC(Cc1ccccc1)c2ccccc2
25. Draw the structure of compound G.
OC(=O)C(Cc1ccccc1)c2ccccc2
26. Draw the structure of reagent H in the following transformation:
BrCC=C|ClCC=C|ICC=C
27. Al D. Hyde prepared a sample of 
using
an enamine reaction. Draw the structure of the starting carbonyl
compound that Al selected.
CCC(=O)c1ccccc1
28. Draw the structure of compound J:
CC(=O)C1CCCC1=O
29. Consider the following general reaction:
This reaction would proceed slowest when G = H, CHO, CH3, C6H5 . Enter the formula for your choice of G in the text field for this question.
30. How many nodes would the LUMO of the MO diagram of 
have? 6