I’m working on a chemistry multi-part question and need guidance to help me learn.
Answer the following Questions in the Dehydration Reaction of an Alcohol
1. Draw the complete mechanism you would expect for the reaction of phosphoric acid with
cyclohexanol. Include all major steps and use arrows to show the movement of electrons. What
sort of reaction mechanism is this?
2. Draw the complete mechanism you would expect for the reaction of tert. butyl bromide with
sodium methoxide (NaOCH3) in methanol. Include all major steps and use arrows to show
the movement of electrons. What sort of reaction mechanism is this?
3. Is it the same mechanism as in question 1? Why or why not?
4. When 1,2-cyclohexanediol is dehydrated in the presence of concentrated sulfuric acid, the
major product is not an alkene. Instead, you get cyclohexanone. Write a reasonable and detailed
mechanism for the dehydration of 1,2-cyclohexanediol to form cyclohexanone. Use curved
arrows to show the flow of electrons and draw the structures of all intermediates and byproducts
formed in the course of this reaction as well as any alternative resonance structures that will help
you to account for the formation of the major product observed in this reaction.
5. What compound did you synthesize in today’s experiment? Write the balanced equation for
the reaction.
6. Write the mechanism of acid-catalyzed polymerization of ethylene to polythene.
7. Complete the following sentence by filling in the blanks with the most appropriate words or
phrases: The mechanism of the dehydration reaction involves the initial _______________ of the
alcohol by a strong acid which converts the _______________ group into water, which is a good
leaving group.
8. Which is the rate-determining step for an E1 reaction mechanism?
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