part_1-chap_15_and_16

part_1-chap_15_and_16 - CH 3 C CH 3 CH 2 CH 3 CH 3 + HCl +...

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Part 1. Chapters 15 and 16 1. Draw structures corresponding to each of the following names. (9 pts) a) p -bromobenzoic acid b) 2,4-dichlorophenol c) cumene 2. List the criteria (in order!) that must be met for a molecule to be aromatic. (4 pts) 3. For each molecule below, predict whether the molecule would be expected toshow aromatic character or not. Explain you answer in each case. (8 pts) a) b) N O
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3. Cyclopentadiene is one of the most acidic hydrocarbons known. Its pK a = 16, a value comparable to that of water. Explain why cyclopentadiene is so acidic. (6 pts) H H B H BH + 4. Write the complete stepwise mechanism for the Friedel-Crafts alkylation of toluene with 1-chloro-2,2-dimethylpropane shown below. Show all electron flow with arrows and write all intermediate structures. (8 pts) 5. Draw at least two resonance structures to show why benzaldehyde reacts slower than benzene in electrophilic aromatic substitution reactions. (4 pts) CH 3 H 3 C C CH 3 CH 3 CH 2 Cl AlCl 3
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Unformatted text preview: CH 3 C CH 3 CH 2 CH 3 CH 3 + HCl + C H O 6. Give the major organic product(s) of each of the following reactions. If no reaction is predicted, write "N.R." (3 pts each) a) b) c) d) e) Br I 2 CuCl 2 OCH 3 NO 2 Br 2 FeBr 3 C(CH 3 ) 3 CH 3 KMnO 4 H 2 O C CH 3 O 1. HNO 3 , H 2 SO 4 2. H 2 /Pd NO 2 CH 3 Cl AlCl 3 f) g) 7. Choose the best reagents from the list below for carrying out the following two-step conversions. Place the letter of the reagent in the box beside the reaction number over the arrow. There is only one answer for each reaction. (2 pts each) A. NBS, peroxides B. CH 3 COCl, AlCl 3 C. Cl 2 , AlCl 3 D. NaNO 2 , heat E. Br 2 , FeBr 3 F. HNO 3 , H 2 SO 4 a) b) CH 3 1 equiv. Cl 2 FeCl 3 NBS peroxides Br NO 2 1. 2. 1. 2. Cl C CH 3 O 8. Show how the following synthesis could be accomplished. Give all reagents and the structures of all intermediate compounds. (7 pts) HO 3 S COOH Br CH 3...
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part_1-chap_15_and_16 - CH 3 C CH 3 CH 2 CH 3 CH 3 + HCl +...

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