Chapter 14: 33E (page 447)
Show the structure, including stereochemistry, of the product from the following Diels-Alder reaction:
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Chapter 14: 33E (page 447)
Show the structure, including stereochemistry, of the product from the following Diels-Alder reaction:
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Give the structures of both 1,2 and 1,4 adducts resulting from reaction of 1 equivalent of HCl with 1,3-pentadiene.
Question: 1,3,5-Hexatriene has =258 nm. In light of your answer to Problem
14-48, approximately where would you expect 2,3-dimethyl-1,3,5-hexatriene to absorb?
How can you account for the fact that cis-1,3-pentadiene is much less reactive than trans-1,3-pentadiene in Diels-Alder reaction.
Treatment of 3,4-dibromohexane with strong base leads to loss of2 equivalents of HBr and formation of a product with formula C6H10.Three products are possible. Name each of the three, and tell how youwould use 1H and 13C NMR spectroscopy to help identify them. Howwould you use UV spectroscopy?
The following ultraviolet absorption maxima have been measured:
1,3-Butadiene 217 nm
2-Methyl-1,3-butadiene 220 nm
1,3-Pentadiene 223 nm
2,3-Dimethyl-1,3-butadiene 226 nm
2,4-Hexadiene227 nm
2,4-Dimethyl-1,3-pentadiene 232 nm
2,5-Dimethyl-2,4-hexadiene 240 nm
What conclusion can you draw about the effect of alkyl substitution on
UV absorption maxima? Approximately what effect does each added
alkyl group have?
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