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Practice Exam 3 (100 Points) Disclaimer: this practice exam is not a mirror image of the actual test nor does it contain all the material you will be tested on (please see the exam study guide on testable material). The aim here is to help you become familiar with test format and the type of questions you will be asked. 1. Name the following compounds O O Br HO O Isopropyl butyrate (1-methylethyl butanoate) 4-bromobutanoic acid O O OH O 2,4-dimethylbenzoic acids Cyclobutyl propionate 2. Draw the structure of the following compounds a. 3-methylpentanoic acid O OH b. Methyl-3-cyclohexylpropanoate O O 3. Identify the following as a hemiacetal or acetal hemiacetal acetal hemiacetal 4. Rank in increasing order the boiling points trends you would expect for alcohols, alkanes, ketones and carboxylic acids. Provide rationale for your ranking. Carboxylic acid > alcohol > ketones > alkanes The ranking is based on the ability of these compounds to form hydrogen bonds (their attractive intermolecular forces). Carboxylic acids can form two hydrogen bonds (they are dimmers), followed by the monomeric hydrogen bonding between alcohols. Ketones can’t hydrogen bond but have electronegative oxygen and alkanes lack intermolecular forces. 5. Provide synthetic route for the following organic compounds, starting with the started material and show all intermediate steps a. 3-methylpentanoic acids starting with an alcohol and show all intermediate reactions. O O [O] [O] OH OH H 3-methylpentanoic acid b. Butyl acetate from appropriate alcohol and acid O OH 1-butanol + HO acetic acid O O butyl acetate 6. Succinic acid is an intermediate in the citric acid cycle. The structure of succinic acid is shown below. Provide two compounds that you could oxidize to form succinic acid and show their reaction O OH HO O 1. Starting with an aldehyde O O H Excess H [O] OH HO O O 2. Starting with an alcohol O O Excess Excess OH H OH HO [O] H HO [O] O O 7. Predict the product(s) that forms in the following reactions O O + NaOH O + O Na OH HO O + + + H H 2O + H3O+ O O O H2N O + NaOH O H2N Na+ HO O