Dolbier HW Solutions 252 - sp-hybridized and the bonding is...

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10.33 Compare the mirror-image forms of each compound for superposability. ( a ) Rotation of the mirror image 180 ° around an axis passing through the three carbons of the C ? C ? C unit demonstrates that the reference structure and its mirror image are superposable. 2-Methyl-2,3-hexadiene is an achiral allene. ( b ) The two mirror-image forms of 4-methyl-2,3-hexadiene are as shown: The two structures cannot be superposed. 4-Methyl-2,3-hexadiene is chiral. Rotation of either representation 180 ° around an axis that passes through the three carbons of the C ? C ? C unit leads to superposition of the groups at the bottom carbon but not at the top. ( c ) 2,4-Dimethyl-2,3-pentadiene is achiral. Its two mirror-image forms are superposable. The molecule has two planes of symmetry de fi ned by the three carbons of each CH 3 CCH 3 unit. 10.34 ( a ) Carbons 2 and 3 of 1,2,3-butatriene are
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Unformatted text preview: sp-hybridized, and the bonding is an extended version of that seen in allene. Allene is nonplanar; its two CH 2 units must be in perpendicular planes in order to maximize overlap with the two mutually perpendicular p orbitals at C-2. With one Reference structure C C CH 3 H 3 C H 3 C CH 3 C Mirror image C C CH 3 H 3 C H 3 C CH 3 C Reference structure C C CH 2 CH 3 H 3 C H 3 C H C Rotate 180 8 C C H 3 C H C Mirror image CH 3 CH 2 CH 3 Reoriented mirror image C C H CH 3 C H 3 C CH 2 CH 3 Rotate 180 8 Mirror image C C CH 2 CH 3 H H 3 C CH 3 C Reoriented mirror image C C H CH 3 CH 2 H 3 C CH 3 C 2-Methyl-2,3-hexadiene and Reference structure C C H CH 3 CH 2 H 3 C CH 3 C Mirror image C C CH 2 CH 3 H H 3 C CH 3 C 246 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS...
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