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FraenkelMT2prac - “QM/Md E Quay/low 2 Complete the...

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Unformatted text preview: “QM/Md E Quay/low 2. Complete the following reactions filling in the missing reagents, reactants or products. 0 II (a) CH3COH + KEB 0He S 0 II II heat (b) CHZCCHZCOH H 0 II (c) (CH3)3CCO e ng N Br2 H3C J/ (d) Cf / H + Ph3P=O N 9 OCH \/ (C) ‘7 N 3 + H20 OCH3 ‘3 ‘EH3 “3 “—6 eO—S—C—O—H Na$ / H20 u I o fHZ CH3 2 Page 2 Total J (i) Ph3P + CH3CHZI N O 4 II J (j) PhCCH3 + PhMgBr N J (k) N (CH3CH20)4A19 Lie / a) (CH30>4BeNa$ ¢> He L G / (m) K6 OH O + N2 HOCHZCHZOH HQ (0) (:LO N H20 + NH2 N 3 Page '3 Total bélanged. H / 0\ [H (a) C=C h» / \ H—O H 0 b g + H63 5» U CH3/ ‘CH3 Ph Ph\ l ,Ph 0 CH3 9 (d) Ke \C—N=N—H + H20 _____, / Ph $Hs eN_CH3 Cg 5.9 H CH§ CH3 _O/H (g) ,0 + > e H CH3 Page 4 Total 6. Road map (2 pt. each). On the basis of the following information obtain the structures of A-I. E HO EC :1 NDE» K990He Mg HOCHZCHZOH ether C PhaP G F CH3Li H€D HzNNHz HBr HONH2A 1 LiAlH H 2.H+, H20 V A CIO3 I H2, Pt 1. 03 S S 2. CH3SCH3 A Clues: G is a phosphonium salt. H is a bromide. A appears three times. WRITE YOUR ANSWERS ON PAGE 8. 1. Name the following compounds (2 pt. ea). (a) CH3CHCH2CH3 I :_QH (b) W (C) (CH3)3N: :o : u (d) CH3CH2CH2CH2COH 202 (e) . O' (h) GI R . . . . ,Rl (D \N’N=C\ Pl R2 (generic name) R1 (g) c u H R2 Q‘H (generic name) lactone (fill in the rest) Page 1 Total N 2. Complete the following steps in different mechanisms, BALANCED (3 pt. ea) 9 H /. “A (a) (CH3)3CCH2—O\. H (not loss of H+, rearrangement) . H “of :o: O. I 00".. (b) H29 + H—Cli—QfirQH CH3IO: 101 (c) H (9... CH3CC1: + .9H N IQ . // =1.“ “9 (d) CH3N.H2 + :o: I I . - J N Q. (rearrangement) H H B_r: (0 i H '9 (h) (CH3)2'NH + 1:C:l—:ClI‘—> PageZTotal K 3. Complete the following reactions by filling in the missing components - reactant(s), reagent(s) or product(s). Some reactions may not go at all (2 pt. ea). <a> mm N \H Na 31He .I.e e (b) N (CH3)3CQ. K + H2 K2CI'207 3 c CH CCH OH R» Cr+ + () ( 3)3 2 H29, H63 39129 CH3 ((1) .. ; Cl H (CH3)3C9. =9 KGB Br 3 .- e a mu IBrI Na (6) Nae) :QHe 2:87: + .. + H29. No2 (f) + CH3¢j: A1C13 Page 3 Total (CH3)3CHNH2 C02 C12 E» e I C e (p) base Na 2912 4. Electronic structure and properties. , , ' °,H o’H Q. B , \ N C :0\H H o o H H H o o (a) Which compound has the lowest boiling poin (2 pt. )? Circle the capital letter A, B or C. (b) Name the effect reponsible for your answer (2 pt.). R (c) Draw a diagram to illustrate your answers in (a) and (b) ( 2 pt.). Page 5 Total \ ...
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