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Chem112BExam__2_key

Chem112BExam__2_key - Chemistry 1123 Midterm 2 Thursday...

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Unformatted text preview: Chemistry 1123: Midterm 2, Thursday April 12, 2007 Name: #— UCSID: _____________ 051: Question 1 Question 2 Question 3 Question 4 Question 5 Question 6 Question 7 Question 8 Total ——/175 points Question 1 Predict the products of the following reactions. 50 (a) 3M0 H2 “ b. 3 of the possible products I-moa A (6 points) M1 . SMe 5 ,SW m1 -_ 'I 01“” : 61” Major Product O—COCI -_—y AlClg, CH2C|2 0a; (4 points) Question 2 How would you make Cl (11) from G Et 6 1 (15 points) E o T HznlNH-L | KOH (:7 “LN/W3 (I: V 7 ? F903 CI. 0" - 7 E 6/ (b) Q/J\ from G (15 points) MH I —-.._....__> k- ”2.50:. We L. 0t- ' r ———_b v I z Question 3 . (a) The following molecules may be constructed using the Diels-Alder reaction. For each compound. show the components for assembling the Dials-Alder adduct. (5 points each) .— a... H 3(b) Propose structures for A and B to make the Wieland-Miescher ketone using a Robinson Annulation. Propose a synthesis to make C from the Wieland-Miescher ketone keeping in mind the gaseous byproduct and the Diels-Alder reaction. (20 points) o 0 £- + :5 <= 0 0 o Wlohnd-Mleecher Kenna A B O L A! *4 OI #- Hi i LI 14' H150 L1 ,. v —- 7 - o [4-0 H- , N \‘L—M 0r dr (oz Question 4 The following compounds A and C undergo protonation to form cations B or D, respectively. Show the corresponding cations and explain why they are preferentially formed over other cations in 25 words or less with appropriate figures. (10 points) H" B /W '—"—" (Cation) A H" D %I: —.'- (canon) C fl -———~”* > sh \ a .r A/T A/T “Hull rt (yr-Liam ( (EA resuming 9+a1tufilx'1iea H H .+ C 1...; E % &\’ fits-<9] qllvl‘l-L C01 +01 (- D‘ rfbiJNnnre Sflfigr'fiilea Question 5 (a) Which of the following reacts faster in a Dials-Alder reaction? Explain your answer with no more than two figures and two sentences. (8 points) Me Me l / Phw / 2v £34,; Ph 5 l‘ .i 6-0? he J l a Ride; m i? (QQEM PH)?“ @ 6ib1cqvor91, baa on “it” in Sinful; (b) Which of the following is more acidic? Explain your answer with no more than two figures and two sentences. (8 points) nu orE'ia-il OUQF l'C’l p 90.16, of‘lo- lqu 0U QC lqe (c) Which of the following is more acidic? Explain your answer with no more than two figures and two sentences. (8 points) \L- W — Hi ‘1} CD non «mini-L WWW/lire Question 6 State whether the following compounds are aromatic, antiaromatic or neither. Explain your rationale using resonance structures or confomiational depictions where appropriate to support your answer. (4 points each) J"V anii’mramaim OCH} fgTE/‘ocns ; NJ B 0 ”Either“ mi?” “FWQI‘aMnhc (PLMm- N OI" fie .‘ Jrh-er- Lnon—plqnm \ Question 7 Recall that thionyl chloride. SOClg is a commonly used reagent for making acid chlorides from acids such as A. 0 g 0 CI’ "cn o '————"' Rial-1mm“ Chloride) + varoducta Cflzclz A Use this information to determine a mechanism for the following reaction. (20 points) \L N\L -“ soot2 N I}9H —C-—-+H20l2 c1 1:; "'tCI 93,7 .1 ‘9‘ (b) Why are two products formed in (a)? (5 points) "HQ Wmclwm pf‘oteeéj +Lfirdu‘yfi on okocmrbemqm {‘n‘rermetm‘lfi W‘m‘L‘H (Um. 5?. W**%‘<QL 0n eilho- {:qu Question 8 - Cyclooctatetraene (COT: CgHg) has an interesting conformational structure. (a) Please draw COT and explain why it adopts the observed conformation. (10 points) an L- Nomi-Ft. nmqmnnn 'Lft: (b) Cyclooctadiene, A, is known to adopt a conformation similar to COT. Use this information to provide a mechanism for the transformation shown below (10 points) and draw a three-dimensional structure of an intermediate that accounts for the stereochemistry of B. (5 points) Br Br; —I-- CHZCIQ Br A B ...
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