Ch_322a_10.011

Ch_322a_10.011 - are equivalent and show identical chemical...

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Reactions that Generate Tetrahedral Stereocenters When achiral alkanes react to produce a chiral product with a single tetrahedral stereocenter, a racemic form is obtained. CH 3 CH 2 CH 2 CH 2 CH 3 pentane (achiral) Cl 2 h ! CH 3 CH 2 CH 2 CH 2 CH 2 Cl 1-chloropentane (achiral) + CH 3 CH 2 CH 2 CH Cl CH 3 2-chloropentane (chiral) + CH 3 CH 2 CH Cl CH 2 CH 3 3-chloropentane (achiral) 2-Chloropentane is produced as a racemic form.
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Analysis of the Stereochemistry Structural Symmetry CH 3 -C H 2 -CH 2 -C H 2 -CH 3 equivalent hydrogens Because these are not stereocenters, the two H at each carbon
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Unformatted text preview: are equivalent and show identical chemical reactivity. C C 3 H 7 H H CH 3 The Reaction Pathway C CH 3 C 3 H 7 H H Cl . Removal of either H leads to the same intermediate. C CH 3 C 3 H 7 H . trigonal planar (achiral) Cl 2 Cl 2 (B) (A) C CH 3 C 3 H 7 H Cl (R) C CH 3 H C 3 H 7 Cl (S) Because of the symmetry of the radical intermediate, there is equal probability of reaction by paths (A) and (B), which produces the two enantiomers as a racemic form ....
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Ch_322a_10.011 - are equivalent and show identical chemical...

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