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Solutions_Manual_for_Organic_Chemistry_6th_Ed 93

Solutions_Manual_for_Organic_Chemistry_6th_Ed 93 - 5 1 5(a...

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Unformatted text preview: 5- 1 5 (a) H CI / '- " C == C == C ' ' CI no asymmetric carbons , but the molecule i s chiral (an allene) n o asymmetric carbons ; thi s allene has a plane of symmetry between the two methyls (the plane of the paper), including all the other atoms because the two pi bonds of an allene are perpendicular, the Cl i s i n the plane of the paper and the pl ane of symmetry goes through it; not a chiral molecule H \,\ "H (b) n o asymmetric carbons , but the molecule i s chiral (an allene ) ; the drawing below i s a three­ dimensional picture of the allene in (a) showing there is no plane of symmetry because the substituents of an al lene are in different planes (d) H CI / "- C == C " / / C == C (e) �/ ( f) H H planar molecule-no asymmetric c arbons; not a chiral molecule ( g) "- / H o 0 �JB r Br no asymmetric carbons , but the molecule is chiral due to restricted rotation; the drawing below is a three­ dimensional picture showing that the rings are perpendicular (hydrogens are not shown) HH no asymmetric carbons , and the groups are not l arge enough to restrict rotation ; not a chiral compound " ' -j H p l ane o f symmetry bi sectin g t h e molecule; no asymmetric c arbons ; not a chiral molecule (h) two asymmetric c arbon s ; a chiral compound 86 ...
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