practice_test_1_key

practice_test_1_key - CH 1 18B Practice Midterm Closed Book...

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Unformatted text preview: CH 1 18B Practice Midterm Closed Book and Notes No calculators Problem 1 Provide the reagents necessary to carryout the following transformations: Note for part (e) also provide the structure of X. CH3 \fifii H DBABO 3 N‘NSHH" :1 ———> "OH a) €l Problem 2 Provide the necessary reagents to carry out the following synthetic transformations: (Note: More than one step is necessary for each synthesis!) a) ? Br W” __, A)\ ’X ‘3‘st J A 3) %r b) Problem 3 Propose curved arrow mechanisms for the following two transformations: Hf;(§,—:g‘cl\ ? I (1‘ H20 0 Li’\ A 3‘} H30 2 CH3 ——'—’ ’- 6" u. a) H2304 ‘X 3 ' “ L“ 0‘0 ._H ‘3" \%3l* c“ ~CEC-“Ci‘g Elam“ ~‘ ”A ‘0‘“: 3 Ag 23% 6“: C“ S :3’ 0‘s ’ H5706? H“ H H I)\ J' T Cw.) H ‘ ~ “3 (4—. M (L ‘6 41;, ‘s aflm‘M‘Q Cf? i --Qk\C¥\ “\chnbcfi a < a? fatness (L 0‘31; 3 J fi) A) H\ Q: j A 4‘7?'~H v \ m ”S \ . (New coil Br Problem 4 Predict the major products for each of the following reactions, showing stereochemical relationships where appropriate: 950/0 H2804 (”N )\/\ HBr kfi: V \ / 21) OH d) (i W 03 ——»Z" Milli +S€\\‘i \ CH20I2 CH3COQH / A xi \ -78°C 6) mCPBA /\/\= ——-—> CHC|3 W C) f) _ NaNH2 _ R e , $ ”51“ H-C:C—H —» fi—Ci M \u ‘3 l’roblem 5 What types of changes do most organic molecules undergo upon absorption of a) infrared light Qbfim \> Axix 'S\é C 2 b) radiowaves (in an external magnetic field) m 0 C\('of 59“" §C§fg c) microwaves $4: flax Sic:\( g d) ultraviolet light €\C§;’G‘Ai (f SLES Cg e) visible light ekcfirbfli L $5 3 Problem 6 For each of the reactions shown below, circle the molecule that would be formed in higher yield and explain why the selectivity is observed. 21) H GC=CHCH3 +HBr _> m or ® (I /()'!-—-—C+ib€ix3 We: N M M C“ p A Q; it Q) l t / \/ “\chacig LAC bi» Br Br ...
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