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Unformatted text preview: CHEMISTRY 225 FINAL EXAM, PART I (FREE RESPONSE QUESTIONS) JUNE 25, 2008 NAME QM w(./ b 4 7—" GOOD LUCK! Part I ,1 9.3 (27) MC. '62) 8 [email protected] each= Q7 (4 (98) TOTAL 8 (a 9' (125) COURSE TOTAL (500) EXTRA CREDIT QUIZ (20) COURSE GRADE (27 Points) Answer each of the following questions. The point value of each question is indicated. a. (9) ROADMAP. Demonstrate your expertise as a synthetic organic chemist by providing structures for the unknown compounds in the reaction sequence below. _(CH30H3)2‘?_9; \N' 1‘ Br2 _ I? (CH3CH2)3COH l 2. 2NaNH2 ‘i 0 Choose one of the organic compounds in this synthetic sequence and assign its IUPAC name. Be sure to indicate which compound you are naming! l “ hrs m6 - ‘4 ~M—l/L7 7r<l 43, can b. (6) CONFORMATIONAL AND ROTATIONAL ANALYSIS 0 Complete the conformational equilibrium for the substituted cyclohexane below. 0 Write a structural formula for a bicycltc structural isomer of this compound. 0 Write a Newman projection for 3-methylhexane [looking down the C(3 )-C(4) bond] in which the longest carbon chain is anti. Newman projection c. (7) STEREOCHEMISTRY. 0 Write a structure for the reactant in the brornination reaction below. 0 Convert the product (compound A) to a Fischer projection with the longest carbon chain vertical 0 Assign configurations to the two stereogenic carbons of compound A. 3 a , 4 5 0 Write 21 Fischer Projection for a diastereorner of A “0" 5 r at at; '14» Cit. u r 1 H i?- g} E on: on; compound A ‘5 a? C we 4;? ) Fischer projection Diastereomer - -2- d. (5) ORGO IN SPACE. According to a report in the June 16 issue of Chemical & Engineering News, astronomers have discovered the molecule aminoacetonitrile (structure below) in interstellar space. Aminoacetonitrile is a precursor to the amino acid glycine. o Directly on the structure of aminoacetonitrile write in all lone pairs. 0 Determine: the geometry at Na. vaa w. (i a. i o the hybridization at C1, 0 Complete the reaction to demonstrate that an aqueous solution of aminoacetonitrile has a pH greater than 7.0 H ‘9 I I-FNa—tf—CtaN’i + H20 1 H H aminoacetonitrile es (3) BONUS QUESTION! As reported in the June 2 issue of Chemical & Engineering News Israeli scientists have found that incensole acetate, a natural product isolated from frankincense resin, is psychoactive in mice. The structure of incensole acetate is shown to the right. 0 Identify the circled functional group to tie ., 0 Circle an isoprene unit in the structural formula of incensole acetate. incensole acetate 0 Determine the molecular formula of incensole acetate C 2 2 H 3g 03 ...
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