Isomers on Page 156 of the OBook

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kshalbi
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Isomers on Page 156 of the OBook

Postby kshalbi » Tue Feb 23, 2016 6:28 pm

Page 156 of the organic textbook says that the carbocation has a trigonal planar geometry and so the nucleophile can approach from either side and result in two possible isomers as products. What does the text mean by "either side"? From the picture, it looks like the carbocation is just flipped, but the nucleophile attaches between the H and the H3CH2C group in both of them. Also why doesn't the nucleophile attach between the H and CH3 group or the CH3 and H3CH2C groups?

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Re: Isomers on Page 156 of the OBook

Postby Chem_Mod » Wed Feb 24, 2016 12:17 pm

This is a graphical depiction of what the book means. Depending on which face the nucleophile attacks from will result in different stereochemistry of the product.

IMG_9656.JPG

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Re: Isomers on Page 156 of the OBook

Postby Chem_Mod » Wed Feb 24, 2016 12:46 pm

Also, the two other options that you asked about are all the same as the first option you stated. The nucleophile is attacking the central carbon of the molecule (well the p orbitals of the cation on the carbon, but essentially the carbon is where it attaches).


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