Chapter 6: Q14P (page 300)
Predict the major product of the following substitutions.
Short Answer
Answer
Chapter 6: Q14P (page 300)
Predict the major product of the following substitutions.
Answer
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Get started for freeStrawberry growers have used large quantities of methyl bromide (b.p. 4ยฐC) 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. 43ยฐC) 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?
Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.
Draw the structures of the following compounds.
(a)sec-butyl bromide
(b)isobutyl chloride
(c) 1,2-chloro-3-methylpentane
(d) 2,2,2-tribromoethanol
(e) trans-1-bromo-2-methylcyclohexane
(f) methylene bromide
(g) iodoform
(h) 1-bromo-1-isopropylcyclopentane
(i) tert-pentyl bromide
When water is shaken with hexane, the two liquids separate into two phases. Which compound is present in the top phase, and which is present in the bottom phase? When water is shaken with chloroform, a similar two-phase system results. Again, which compound is present in each phase? Explain the difference in the two experiments. What do you expect to happen when water is shaken with ethanol (CH3CH2OH)?
(b)In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that in part (a) does not occur.
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