quesitons10_fa10_ans - H 2 /Pd on C Cl O Cl Cl 2 AlCl 3 (or...

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Questions 10 December 2, 2010 1. Which of the following molecules are (is) aromatic? Note: lone electron pairs are not shown explicitly . C is not aromatic N N N B N B N B N P N P N P N As a) b) c) d) 2. Which of the following is not aromatic? D is not aromatic 3. There is something wrong with the following syntheses. What is it? Are there any other possible routes? 1. CH 3 CH 2 CH 2 Cl/AlCl 3 2. Cl 2 /FeCl 3 Cl Cl O CN O 2 N 1. CH 3 CH 2 COCl, AlCl 3 2. HNO 3 /H 2 SO 4 Cl CN The first reaction has a deactivating group on the ring so the F/C’s will not work; Acidic conditions would hydrolyze the –CN. There is no easy route to this molecule with reactions you know. The second has rearrangement problems and the Cl is an o/p director. Better path: do a F/C acylation; separate isomers (you want the para chloro one); chlorinate; and reduce the
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ketone: (or Wolff- Kishner, Clemmensen)
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Unformatted text preview: H 2 /Pd on C Cl O Cl Cl 2 AlCl 3 (or FeCl 3 ) Cl O AlCl 3 Cl O Cl 4. Complete the following reactions: + para isomer O Ph O the activating group directs the position of substitution OCH 3 Cl OCH 3 Cl CO 2 H CO 2 H KMnO 4 H + OCH 3 Cl CH 3 CH 2 CH 2 Cl AlCl 3 O CH 3 CH 2 COCl AlCl 3 5. The sulfonation reaction is reversible. Show the mechanism for the desulfonation reaction: + SO 3 H S H O O OH OSO 3 H H SO 3 H 6. Propose a synthesis of the following molecule using benzene or phenol as the source for aromatic rings. Any other reagents may be used as needed. It is a larvicide that is selective toward mosquito larvae. C CH 3 CH 3 OH C(CH 3 ) 3 C(CH 3 ) 3 product 2 (CH 3 ) 3 CCl AlCl 3 OH phenol/AlCl 3 (AlBr 3 ) Br NBS hv/CCl 4 (CH 3 ) 2 CHCl AlCl 3...
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quesitons10_fa10_ans - H 2 /Pd on C Cl O Cl Cl 2 AlCl 3 (or...

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