Chapter 14: 25Ea (page 447)
Give IUPAC names for the following compounds:
(a)

Short Answer
3-Methyl-2,4-hexa-diene
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Chapter 14: 25Ea (page 447)
Give IUPAC names for the following compounds:
(a)

3-Methyl-2,4-hexa-diene
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The following model is that of an allylic carbocation intermediateformed by protonation of a conjugated diene with HBr. Show the structureof the diene and the structures of the final reaction products.

How could you use Diels-Alder reactions to prepare the following products ? Show the starting diene and dienophile in each case.
a)

1,3-Cyclopentadiene polymerizes slowly at room temperature to yield
a polymer that has no double bonds except on the ends. On heating, the
polymer breaks down to regenerate 1,3-cyclopentadiene. Propose a structure for the product.
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?
Dimethyl butynedioate undergoes a Diels-Alder reaction with (2E,4E)-2,4-hexadiene. Show the structure and stereochemistry of the product.

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