Ch_322a_8.05

Ch_322a_8.05 - with equal probability . (A) (B) C H CH 3 CH...

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Stereochemistry of Ionic Additions to Alkenes In many addition reactions, stereocenters are formed producing chiral compounds from achiral alkenes: CH 3 CH 2 CH=CH 2 1-butene achiral + HX CH 3 CH 2 CHCH 3 X * 2-halobutane chiral In such reactions, a racemic form is necessarily produced.
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A Closer Look at the Stereochemical Result Step 1: Electrophilic Addition C=C H CH 3 CH 2 H H achiral (plane of symmetry) + HX C-CH 3 H CH 3 CH 2 + sec-butyl cation achiral (plane of symmetry) + X - Step 2: Nucleophilic Addition C-CH 3 H CH 3 CH 2 + + X - Path A Path B Because of the symmetry of the carbocation, paths A and B occur
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Unformatted text preview: with equal probability . (A) (B) C H CH 3 CH 2 CH 3 X (R)-2-halobutane (50%) C H CH 3 CH 2 CH 3 X (S)-2-halobutane (50%) A Racemic Form Quiz 8.05 Predict the products of the following addition reactions. Indicate important stereochemical details in the products. CH 3 CH 2 CH 2 CH=CH 2 + HI CH 3 + HI CH 3 CH 3 + HI CH 3 CH 2 CH 2 CHICH 3 as a racemic form CH 3 I achiral + CH 3 CH 3 CH 3 CH 3 I I H H two diastereomeric products, each as a racemic form...
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Ch_322a_8.05 - with equal probability . (A) (B) C H CH 3 CH...

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