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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
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