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filling organic chemistry prelab
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CHEM 242L
Exp. 5 Pre-Lab / Grignard and Dehydration Reactions
Name:_________________________________
Score:______/ 10
1. Using line-bond structures draw a complete and concise reaction scheme. Include only the essential
reagents. Under each structure write the molecular formula and molecular weight. Label each alkene isomer
as either kinetic or thermodynamic.
2. Draw the mechanism for each major chemical transformation. (Hint: Refer to your text for the mechanistic
details of the Grignard reaction and acid catalyzed dehydration of alcohol.)
3. Calculate the theoretical yield for each chemical reaction and show all calculations.
4. Briefly state the objective for each step in the experiment and how the outcome of each step will be
determined. What should you see in the data to prove the identity of the alcohol formed during the Grignard
and the alkenes formed from the dehydration of the alcohol? For example, how many 13C and 1H NMR
absorbencies and what molecular weight should be observed in the MS. What functional groups and
frequencies would you expect for the IR?
5. During Part 2 of the experiment (dehydration reaction), drops of the reaction mixture are placed in a test tube
containing dichloromethane and 10% aqueous sodium bicarbonate solution at 5 minute intervals? The sodium
bicarbonate neutralizes the acid catalyst. Why is it important to neutralize the acid catalyst?
6. What difference do you expect to see between the first and final samples taken during the dehydration
reaction?
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