CHM234f'07E1A

CHM234f'07E1A - I Circle the best answer for the following....

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Unformatted text preview: I Circle the best answer for the following. Circling more than one answer will result in zero credit (10 points) A. What is the kinetically controlled product in the following reaction? H31”, -8000 M —-—-—I- \ G) W 2) \A 3) m 4) \f\ Br Br Br Br B. Cyclopentadiene is unusually acidic for a hydrocarbon. Why? 1 Cyclopentadiene is aromatic. e conjugate base of cyciopentadiene is aromatic. 3) Cyclopentadiene is an unstable diradical. 4) The conjugate base of cyclopentadiene is an unstabie C. Identify the correct IUPAC name of the compound below? 0 1)4—benzyl-5-methylhexanal 3 2—methyl-3-phenylhexanal 2) 5-isopropyl-5-phenylbutanal @ -mcthyl-4-phenylhexanal D. Which one of the following is not a resonance form of the cyclohexadienyl cation intermediate in the bromination of benzene? HBr HBr H Br H Br E. Which isomer of dichlorobenzene gives a single mononination product? 1) ortho 2) meta @iara 4) none of them 11 Complete the following reactions. Be certain to indicate stereochemistry in your products (with dash and wedge bonds) if it is important. (35 points) OCH3 (c+13}zc=o|-42 H2304 1. CH3COCI,AICI3 2. H20 3. HN03, H 04 4. Br, FeBr3 IIIA. Provide a mechanism for the following reaction. For fill] credit, clearly show all intermediates formed during the reaction including proper charges. Indicate electron flow using arrows. (12 points) CH3 / H2304 CHZCHa B. Ten milligrams of a compound of molecular weight 240 is dissolved in 10 mL of 95% ethanol, and the solution is poured into a 1 cm UV cell. The UV spectrum is taken, and there is an absorption at law = 327 nm. The maximum absorbance at 327 nm is 0.65. Calculate the value of e for this absorption. (08 pts) “Ema: O'Ola A: é'C'L mm: 2140 6:13. 1 _5 CL no Ul: mole-3t 72%: LNGKED moi-vb é : 0‘65" ammo—5 cm: umm’g-_ u texto*3mim/i,ir 73:51“ * ‘3' ‘5“ n? C. Classify each of the following structures as aromatic, antiaromatic or nonaromatic (10 points) IVA. Provide a scheme for the synthetic conversion shown below. You may employ any reagents, solvents, etc. in your sequence of reactions, but you must start with benzene. (10 points) $f\/ 61/31 OK/ Br F CL > (/0 Er}, , wig; \ A103 {flag HCL @ “L0 151 N O 1.... p N 03 - "O HvSOu 5‘! NB. Write the structure of the diene and dienophile needed to prepare each of the following Diels —Alder product. (08 pts) I 1 3+ “:30 CI $500001, 0 + C2,)l\ooou.t‘3 V. Sketch the molecular orbitals for 1,3,5—hexatriene. Indicate how many electrons are preSent, and in which orbitals. (7 pts) " ...
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CHM234f'07E1A - I Circle the best answer for the following....

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