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Name: ____________________________ Chemistry 102, NSCC, Exam II EXAM 2 (100 pts) Tuesday, May 8th, 2007 1. (15 pts, 5 pts each) Name the following compounds OH O Cl O H OCH3 OH Br 2. (15 pts, 5 pts each) Draw the structure of the following compounds a. 2-methoxy-2,3-dimethylbutane (problem 13.16, part d) b. 3-fluoro-2,4-pentanedione c. 5-bromo-2-pentanethiol 1 Name: ____________________________ Chemistry 102, NSCC, Exam II 3. (30 pts) Parts A to C of this problem refer to an alkane, a ketone, and an alcohol of similar mass, each containing four carbons or less and the indicated molar mass. a. (16 pts) Fill out the table below, ranking the compounds based on their boiling points [1 = highest, 3 = lowest]. Also indicate their solubility in water as either soluble or insoluble Compound Alcohol Molar Mass (g/mole) 60 Alkane 58 Ketone 58 Boiling Point Ranking Solubility in Water b. (8 pts) Based on the molar mass of each compound, what are their respective IUPAC names? (use the back pages as scratch paper or the space below) Compound Alcohol Molar Mass (g/mole) 60 Alkane 58 Ketone 58 Name of the compound c. (6 pts) Based on your boiling point ranking in part A, would you expect ketones to have higher, lower, or similar boiling point then alcohols of comparable masses? Provide Rationale for your answer. 2 Name: ____________________________ Chemistry 102, NSCC, Exam II 4. (20 pts) (Problem 14.63c) Complete the missing steps in the reaction below and name the final product O CH3 CH2 CH2 C H H+ H2 structure 2 (6 pts) heat Pt structure 1 (6 pts) light Br2 Structure of final product (4 pts) Name of final product ( 4 pts) 5. (20 pts) Using a combination of the reactions we have studies so far, indicate how you would prepare the following, starting with the substances given and showing all the intermediate steps. O CH3 C CH2 CH2 H O CH3 CH2 CH2 OH CH3 C CH3 O CH3 C CH CH3 3 C CH3 Name: ____________________________ Chemistry 102, NSCC, Exam II EXTRA CREDIT 6. (4 pts) [Problem 13.63] A compound with formula C4H8O is synthesized from 2-methyl-1propanol and oxidized easily to give carboxylic acid. What is the structure of the compound? 7. (3 pts). Write the isomers of the carbonyl compounds of C3H6O (that is all the isomers you draw must have a carbonyl group in them). 4