Quiz on Alkyl Halides

Missing Organic Reagents

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Copyright Linda M. Sweeting 1997

These problems are organized by chapter number, with the lowest chapter number first (the references will give you a hint as to whether you have learned about a reaction yet, and provide you a source of information if you don't understand). You cannot put the answer into the computer yourself, so keep paper and pencil handy. After you have proposed a compound, click with the left mouse button on the simulated button that says "Answer" to see if you are right or not. In most cases only the alcohol and reagent are shown and you must select a non-alcohol starting material or product. In the computer solutions to the problems, only the largest organic product is shown.

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McMurry 6.8,6.9, Fessenden 10.6, Schmid 7.8 - 7.17

McMurry 7.5, Fessenden 10.9, Schmid 8.1 - 8.4
McMurry 10.10, Fessenden 10.10, Schmid 8.8

McMurry 7.3, Fessenden 10.10, Schmid 8.9
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McMurry 8.8, 8.9, 8.10 Fessenden 10.4, Schmid 9.10

McMurry 10.8, 10.10 Fessenden 7.3D, 13.4D, Schmid 11.7
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Reference McMurry 7.1, 10.7, 17.7, Fessenden 7.4 - 7.6, Schmid 11.17, 12.10, 12.16

McMurry 10.7, Fessenden 7.5, Schmid 11.17

McMurry 11.10, Fessenden 5.4 - 5.5, Schmid 12.1, 12.2

McMurry 11.21, 24.6, Fessenden 5.7, Schmid 12.2 - 12.4

McMurry 11.10, 11.13, 11.15, Fessenden 5.7 - 5.8, Schmid 12.12 - 12.15

McMurry 11.14, 11.15, Fessenden 5.3, 8.2B, Schmid 13.8C

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McMurry 19.12, Fessenden 13.5, Schmid 14.16, 14.17

McMurry 5.1, 5.6, 7.5, Fessenden 10.6, Schmid 18.5 - 18.6

McMurry 7.5, Fessenden 6.1 - 6.6, Schmid 18.1 - 18.4

McMurry 10.5, 10.6, Fessenden 6.5, Schmid 19.3, 20.9A
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Reference McMurry 24.6, Fessenden 5.10, 18.4, Schmid 22.8
2
HINT: Same reaction as with Grignard if ether solvent concentration is not adequate.
Note that aryl halides do not undergo any of these reactions except those with metals, e.g. the Grignard reaction. Nucleophilic aromatic substitution only occurs on rings with strongly electron-withdrawing substituents (McMurry, 10.9, Schmid 23.2, 23.3).

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