R acetoneacers have no prohlas ausilaneeosfasym

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Unformatted text preview: acers have no prohlas ausilaneeosfasym-cquets as If ou a olef h n ot? T d w answer i slf, you eithe pl y yanohydrin b em p ng th me ra metry running have to play heamght-handed manner, or gcuts ltd of central ciarbon ded tennisOlHyerndnd Nodroups nis players of through t in ri olecule. This plane et ho he a set r ght-han and the p a a s a C m g ern ten of left-handed golf clubs. Golf clubs are clearly therefore either chirality sometimes swap the racquet from hand to in half and has chne lmhey cangexist as either of two enantiomers. You o ira ; t ethyl roup on each side. hand. Look at a tennis racquet: it has a plane of can tell this just by looking at a golf club. It has no plane of symmetry, so it must be chiral. But left-handed tennis HO CN plane of symmetry HO CN runs through central carbon, Me Me Me Me OH and CN acetone cyanohydrin symmetry, so it’s achiral. It can’t exist as two mirrorimage forms. Claydon, Greeves, Warren, and Wothers : Organic Chemistry, 2001 On the other hand, the aldehyde cyanohydrin has no plane of symmetry: the plane of the paper has OH on one side and CN on the other while the plane at right angles to the paper has H on one side and RCH2 on the other. This compound is completely unsymmetrical and has two enantiomers. • Planes of symmetry and chirality • Any structure that has no plane of symmetry can exist as two mirror-image forms (enantiomers) • Any structure with a plane of symmetry cannot exist as two enantiomers HO CN R H This statement is, in fact, slightly incomplete, but it outlines such a useful concept that for the time being we shall use it as a valuable guideline. •...
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