BackAn unknown alcohol with a molecular formula of C7H14O was oxidized to an aldehyde with HOCl. When an acidic solution of the alcohol was distilled, two alkenes were obtained. The alkene formed in greater yield was determined to be 1-methylcyclohexene. The other alkene formed the original un-known alcohol when treated with BH3/THF followed by H2O2, HO-, and H2O. Identify the unknown alcohol.
Compounds containing deuterium (D = 2H) are useful for kinetic studies and metabolic studies with new pharmaceuticals. One way to introduce deuterium is by using the reagent LiAlD4, equivalent in reactivity to LiAlH4. Show how to make these deuterium-labeled compounds, using LiAlD4 and D2O as your sources of deuterium, and any non-deuterated starting materials you wish.
(b) CH3CD2OH
When LiAlH4 reduces 3-methylcyclopentanone, the product mixture contains 60% cis-3-methylcyclopentanol and 40% trans-3-methylcyclopentanol. Use your models, and make three-dimensional drawings to explain this preference for the cis isomer.
In which step(s) of the hydride reduction of an ester does the compound undergo reduction? (Hint: Count the bonds to oxygen.)
Propose a mechanism for the reduction of octanoyl chloride by lithium aluminum hydride.
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(d) Ph2CHOH
(e) PhCH2OH
(f) PhCOOH
Show how you would synthesize the following alcohol by reducing appropriate carbonyl compound.
(d)
Show how you would synthesize each compound, starting with an ester containing no more than eight carbon atoms. Any other necessary reagents may be used.
(i) HO–(CH2)8–OH
Suggest carbonyl compounds and reducing agents that might be used to form the following alcohols.
(c) 1-phenylbutan-1-ol
(d)
Show how this 1° alcohol can be made from the following:
(c) a 7-carbon aldehyde
(d) a carboxylic acid
Predict the products you would expect from the reaction of NaBH4 with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(e)
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(e)
Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).
(j)
Predict the products you would expect from the reaction of LiAlH4 followed by hydrolysis with the following compounds. You may assume that these reactions take place in methanol as the solvent.
(d)
Predict the products of the following reactions:
(a)
(b)