Chapter 10: Q19P (page 520)
Show how you would synthesize the following alcohols by adding Grignard reagents to ethylene oxide.
- 2-phenylethanol
- 4-methylpentan-1-ol
Short Answer
a.
b.
c.
Chapter 10: Q19P (page 520)
Show how you would synthesize the following alcohols by adding Grignard reagents to ethylene oxide.
a.
b.
c.
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Get started for freePropose a mechanism for the reaction of acetyl chloride with phenylmagnesium bromide to give 1,1-diphenylethanol.
The following compounds are only slightly soluble in water, but one of them is very soluble in a dilute aqueous solution of sodium hydroxide. The other is still only slightly soluble.
(a) Explain the difference in solubility of these compounds in dilute sodium hydroxide.
(b) Show how this difference might be exploited to separate a mixture of these two compounds using a separatory funnel.
Ever since the Grignard reaction was discovered to react with ethylene oxide, chemists have experimented with other epoxides to test the limits of this reaction (which chemists call the scope of the reaction). The conclusion is that the success of the Grignard reaction is limited by the steric hindrance in the epoxide. One group published results of several Grignard reagents on one epoxide; one of their products is shown here. What Grignard reagent and what epoxide were used to make this compound? Comment on the steric requirements of the epoxide and the stereochemistry of the product.
Show how you would synthesize the following alcohols by reducing appropriate carbonyl compounds.
a. Heptan-1-ol (b) Heptan-2-ol (c) 2-methylhexan-2-ol
b.
Vinyl alcohols are generally unstable, quickly isomerizing to carbonyl compounds. Propose mechanisms for the following isomerizations.
(a)
(b)
c)
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