Chapter 6: 6-22P (page 312)
Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.
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Predict the major product of the following reaction, and give a mechanism to support your prediction.
For each pair of compounds, predict which one has the higher molecular dipole moment, and explain your reasoning.
(a) ethyl chloride or ethyl iodide
(b) 1-bromopropane or cyclopropane
(c) cis-2,3-dibromobut-2-ene or trans-2,3-dibromobut-2-ene
(d) cis-1,2-dichlorocyclobutane or trans-1,3-dichlorocyclobutane.
Strawberry growers have used large quantities of methyl bromide (b.p. 4°C) to sterilize the soil before planting their crops. Like some of the freons, methyl bromide can diffuse up into the stratosphere, where it damages the protective ozone layer. Agricultural chemists have suggested using methyl iodide (b.p. 43°C) as a replacement for methyl bromide. Why is methyl iodide likely to be more toxic to agricultural pests (and people) than methyl bromide? Why is methyl iodide less likely to reach the stratosphere than methyl bromide?
Question: Propose mechanisms to account for the observed products in the following reactions.
Question: For each of the following compounds,
a)
b)
c)
d)
e)
f)
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