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2005 test1A - Chemistry 2203/7(1)5 Test 1A Name Marks are...

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Unformatted text preview: ' Chemistry 2203/7 (1)5)- - Test 1A Name: Marks are in parentheses I 1 (6) For molecules below, provide a systematic name and indicate with an arrow which sp3 carbons are primary, secondary, tertiary and quaternary. . I 0 c» 1" - <4 5 o I 2 5 tr - _ — i2 2. r; o i D f”: 3 _ 3 a 2. Qt R~dornefh l m: GM 3ymcfkg’qw I’Pbiefle J .3 P f’ . 2a (1) Conformational Properties: Draw a Newman projection of ethane in the staggered conformation. H ' H H H if H 2b (1) Give the two factors contributing to the thermodynamic instability of cyclopropane rings. H H i 1! é -1Lorgx?na,€ effcbém (Jack/orig: r‘rirg? drunk/n (Land 4,9332% GD 32 (8) Show the reagents necessary for each reaction. ' HBr‘ ‘ 9” —-> W } Kman‘ 0H 0 p335? Got-I r ‘ :: —-—>---.ZCo Kmh 0 y , u ' PH < '7— 3b (8) Show the starting material which would lead to product. . CHI-.1 9. - gnu—CH3 '—‘ 2.23 H “ Her 3:2 /\\ ——> A I. 6 H3 9' ' H102. o H Chemistry 220317 (’05) 7 Test IA Page 2. 3c. (8) Show the expected product(s) for each of the following reaction. 7 N __)H"/Pt /\/ as a on 0 4’" gr: 90H °H H—E'H —?H~EQ She‘s? Woo clam/Taffy 4a. (6) MECHANISM: Draw a mechanism for the following reaction, showing all intermediates, all curly arrows describing electron movement and all charges (if applicable). - 4b. (6) Explain briefly what is meant by Markovnikov and “anti-Markovnikov” addition of water to an unsymmetrical alkene. Use structures to illustrate your answer. . H9 a H o 9” ' £3 --? N Air ’o/V 1? Huck 'Featwe, addu‘tecy- H a a O H éfmll‘i 20::a4mn g 29H; "my H Med’ ‘ 99 W3 6sz M“ > ” @4111— m ._._-—-) W ’— H- _ . Fanfare. mid-113‘»- W JKK/ ' z o“ _ MLJM s7? OH is. Paulina H r '. came 5. (6) Deduction. Compound A with molecular formula M reacts with 2 equiv of H2 over 3 Pt catalyst to give a linear alkane. Calculate the degree of unsaturation of A. What are the possible functional group/ring combinations for A? When oxidized with ozone (reductive workup), A gives the three aldehydic fragments show below. What is the structure of A? Show your reasoning. Show the product of hydrogenation. " 7 i 0 ° ‘ a we zia—Wsz / f 2'")|\H M 0n a”; q H ' 1%)2d; or waxw‘r‘mfi 1T 03 h '2 W§A $“2' O W . ...
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