SampleExamIIIAnswers - STUDENT #: 5km NAME: ‘% fl; £45...

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Unformatted text preview: STUDENT #: 5km NAME: ‘% fl; £45 I ErCApC FLORIDA INTERNATIONAL UN ERSI Q “a. 79M: DEPARTMENT OF CHEMISTRY Dr. Keller EXAM III CHM 2210-02 Fall 1998 - Be clear and neat; a poorly-drawn structure may be misinterpreted. To obtain partial credit, you must show your work. I. NOMENCLATURE: Provide a name for EACH of the following compounds. Where appropriate. indicate the specific stereoisorner as part of the name. [5 points each] - H\ /CH3 0 1 I: = 2 '1- _. _ x‘ '4": CH 3 I" ””CH2CH3 CH3 I H I CH3 CH3CH2 H II. REACTIONS: Supply structures for the lettered compounds in EIGHT of the following reactions. - Indicate a particular stereoisomer if appropriate; [6 points each] @ Ow + 1. BH3 OH —I-— 2. HZOZ/OH' H I . 0304 OH ——""""' H 2. NaHso3 G) c - CH3CH2 CH3 H CHM 2210-02 Fall 1998 Exam III Page 2 0 ll 4‘ MOH + Cl_fi_©_CH3 —I- ———-I- CH3OH 0 D O / \ e DMF 5. CH3-?_CH2 + CH3 F f E A 6. + HBr ——I- + 2H20 O G (C4H331‘2) 1. Hg(OAc)2 OH THF/HZO H ———-———-l-- 2. NaBH4 H CH3CO3H HZO/HG) 8. CH2 ——"'" —-—-————I-- CH369 CHM 2210—02 Fall 1998 Exam III Page 3 Cl ,CHs KOH/n CH —I" CH3 \ (E2) CH3 ROOR >=\ '1‘ I‘IBI _.__—__+ STRUCTURE DETERNIINATION An unknown compound has the formula CfiHm. 1. What is the IHD for this compound? [2 points] 2. When a solution of Br; in CCl4 is added to the unknown, the bromine color disappears. Wha‘ information does this provide about the structure of the unknown? [2 points] 3. The unknown reacts with H; in the presence of Pt to give CfiHu. What information does this provide about the structure of the unknown? [3 points] 4. The following ketone is one of the products isolated from the ozonolysis of the unknown. What is the structure of the mlknown? [3 points] 0 IV. MECHANISMS: Provide a reasonable, stepwise mechanism to explain TWO of the following observed reactions. Remember to show all steps, all intermediate structures; used curved arrows where necessarv to make a sten clear. [3 noints each] ___._.__._...—_.._ -_\____.__._... 1._. _ ___.--.._..- -.__ _— CHM 2210-02 Fall 1998 Exam III Page 4 QQ— CH3 Br CH3 C1 + HBI‘ CH3 CHM 2210—02 Fall 1998 Exam HI Page 5 Br A 4' Q + 0011C! HBI —h Br\/\/\)\ +2H20 0 CH3 IV. SYNTHESIS: In the Space below, suggest a reasonable synthesis for TWO of the following compounds. Use the given starting material(s) as well as any reagents and solvents that you fin necessary. There is no need to Show the mechanisms for any of the reactions that you use. Just the reactants, the reagents, and the products.[8 points each] CH3CH2 a H . “(=C/ _ CH3CI-I2—CECH Synthe31ze / ' \ startmg from H CHZCHZCH3 and CH3CH2CH2Br Oi i OH ynthesize H "" CHZCH3 Starting from CH3CH2_.. CE C _ CH2CH3 H CHZCH3 CH3 OCH3 CH3 3. Synthesize . starting from s and CHSOH HINT: Use a Williamson Synthesis ...
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SampleExamIIIAnswers - STUDENT #: 5km NAME: ‘% fl; £45...

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