Exam%20_2%20Spr%202009

Exam%20_2%20Spr%202009 - Name CHEM232 – Organic Chemistry...

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Unformatted text preview: Name CHEM232 – Organic Chemistry II Spring 2009 Mid‐term Examination 2 This examination is worth 90 points of a possible total of 600 points for this course, and consists of seven questions (plus a bonus question). You are required to attempt all seven questions, but you may not be required to answer all parts of a given question. Where you are not required to complete all parts, you should clearly indicate which of your answers you wish to have graded. Question 1 (12 points). Choose two of the three structures below, and provide a systematic name for those structures. OH OH O HO OH NO2 Question 2 (12 points). Choose two of the three names below, and draw the corresponding structures. (2R,9R)‐9,10‐epoxydecan‐2‐ol 2,6‐dichloro‐4‐methylphenol (S)‐cyclohept‐3‐enol Name Question 3 (18 points). Choose six of the ten reactions below, and predict their outcomes, including any regio‐ and stereochemical outcomes. CO2CH3 + benzene H3CO2C H2SO4 OH ∆ O Br + Br O HCl ether, 0oC RCO3H CH2Cl2/RT 1) Hg(CF3COO)2 + OH 2) NaBH4/Ethanol + Na Na 1) CH3MgBr/ether O 2) H+/H2O CrO3 OH H+/H2O O H 1) NaBH4/ethanol 2) H+/H2O Name Question 4 (14 points). Explain two of the following three observations in terms of structure, thermochemistry or reaction mechanism. (a) The compound dipropyl ether has a boiling point of 88‐90°C, whereas its isomer 1‐hexanol has a boiling point of 156‐157°C. (b) Treatment of 2‐methylcyclopentanol with sulfuric acid yields two alkenes, of which 1‐ methylcyclopentene is the major isomer. H2SO4 OH ∆ (major) + (minor) (c) 2,3‐dimethylbuta‐1,3‐diene successfully reacts with methyl acrylate to generate a cyclohexene derivative, but 2,3‐di‐tert‐butylbuta‐1,3‐diene does not. CO2CH3 CO2CH3 + CO2CH3 + NR Name Question 5 (12 points). Choose two of the three sets of molecules below, and rank them in terms of acidity, highest acidity = 1, lowest acidity = 4. CH3 SET 1 HO HO HO HO Br NO2 N(CH3)2 CH3 SET 2 HO HO HO CH3 CH3 HO F F SET 3 HO HO F F HO F HO F Question 6 (10 points). Nucleophilic substitution is an important reaction of alcohols and ethers. Describe the differences between the nucleophilic substitution mechanisms known as SN1 and SN2. Name Question 7 (12 points). Predict the outcome(s) of the following reaction (including any regio‐ or steroechemical outcomes), and explain the outcome(s) in terms of the relevant reaction mechanism. You must include the reaction mechanism as part of you answer, and may include any additional structures or diagrams to support your answer. HBr OH Name BONUS Question 6 (8 points). Predict the outcome(s) of the following reaction (including any regio‐ or steroechemical outcomes), and explain the outcome(s) in terms of the relevant reaction mechanism. You must include the reaction mechanism as part of you answer, and may include any additional structures or diagrams to support your answer. Cl Br2 FeBr3 ...
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This note was uploaded on 10/28/2010 for the course CHEM 232 taught by Professor Poole during the Spring '09 term at Ball State.

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