CHM 238 - Ch 4 McMurray

CHM 238 - Ch 4 McMurray - Chap 4 Cycloalkanes:...

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Chap 4 Cycloalkanes:
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Cycloalkanes: Molecular formula has two less hydrogens for each ring in structure. n 2n+2-2(#rings) 10 2(10)+2-2(2) 10 18 C H For example: C H C H = H 2 C H 2 C C H 2 CH CH H 2 C C H 2 CH 2 CH 2 H 2 C H 2 C H 2 C C H 2 CH H 2 C CH 2 CH 2 C H 2 H 2 C CH CH CH H 2 C H 2 C H 2 C H 2 C C H 2 C H 2 CH 2 H 2 C H 2 C H 2 C C H 2 C H 2 C H 2 C CH 2 CH 2 CH 2 H 2 C
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Naming Cycloalkanes: For an unsubstituted monocyclic structure, add the prefix cyclo- to the name of the normal alkane of the same number of carbons. cyclobutane cyclopentane cyclooctane
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Substituted Cycloalkanes: Monosubstituted cycloalkanes are easily named by prefixing the name of the substituent to the name of the cycloalkane. propylcyclobutane methylcyclopentane ethylcyclooctane CH 2 CH 3 CH 3
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Polysubstituted Cycloalkanes: 1. With two or more substituents on a ring, the carbons are numbered so that the substituents receive the lowest total of the locant numbers possible. H 3 C CH 3 CH 3 CH 3 1 2 3 4 5 6 1 1 2 4 1,1,2,4-tetramethylcyclohexane
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Cycloalkyl Groups: Substituents consisting of cycloalkyl groups are also relatively common. H 2 C H 2 C CH cyclopropyl group cyclohexyl group cyclopentyl group
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Restricted Rotations in Cycloalkanes: In most cycloalkanes there is some degree of rotational movement available, but not complete rotation about each of the single bonds. CompleteTwist Prevented by rest of ring.
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Geometric Isomers: Because of the restricted rotation, substituents on top cannot be rotated to replace groups on the bottom without exchanging all top and bottom groups. 180° rotation 180° rotation
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The two 1,3- dimethylcyclo- pentanes on the right are different compounds with different physical properties. H
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This note was uploaded on 12/05/2010 for the course CHM 238 taught by Professor Arney during the Spring '07 term at Sam Houston State University.

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CHM 238 - Ch 4 McMurray - Chap 4 Cycloalkanes:...

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