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test2 - ‘ CHEMISTRY 65.2203/7 L‘WPHTEST#2(m a...

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Unformatted text preview: ‘ CHEMISTRY 65.2203/7 L‘WPHTEST #2 (m a) Name: (MARKS) 5, ' 1. (6) 2:. (1) (1) 3a. (8) b. (8) _ FOR EACH OF THE MOLECULES SHOWN BELOW, ASSIGN THE HYBRIDIZATION AND I GEOMETRY OF THE CARBON ATOMS INDICATED BY THE ARROW. ALSO PROVIDE THE SYSTEMATIC NAME or Trivial Name FOR EACH MOLECULE. 4am, W121. 2 H 2. 5f) WWW W - 3' 4etrd~edm£151° ' _7 __3-¥&oomf€xm6. - A. , 1’) 5... dime‘t’kj {7;— I—R-ep‘I'mna I PHYSICAL PROPERTIES: EXPLAIN WHY MOST ALKYL HALIDES ARE NOT SOLUBLE IN WATER. Poor 14-45%? MIA H20 R-X...1H,0/H EXPLAIN WHY t- -butanoI has a HIGHER MELTING PT than n—butanol. MO“ ‘I: 1....) fizflker dtjne :53 Cm proofing-J15" M08; afflm'uve I53:- moépii4y, Fido Aédéé. SHOW THE REAGENTS NECESSARY FOR EACH REACTION: ‘?” *1 soul: _ C35 III CHa—(IIs-'-(II—H —---———- CH3-(|?\-—-'$'-_H H H H H "x u @011 11.. 7, ,H H—c—c-H ---—-——- cfic ~ 11 ' 5R ”I ‘H m ,H LIA-We; Hf," H’H ‘ ._ CH3—C‘—- C-CH3 —-— [c5 yr ngJ-olfowut ’ ‘H CH3 CH3 95+; , _ 1, {27/50) bf H 5! I 7 {2—— (1: fCHZCHRVI ——-- CH3- (CH2)3- “ma—55H 1-; . SHOW THE STARTING MATERIAL WHICH WOULD LEAD TO THE PRODUCTS SHOWN: 1' CH3” CCIL" “QTOH MSCE CH3- cc12- CH3: OTHS III-*6.” m3: $91731? CH3 ‘? CH3-CH --CH3 + Hz 0H ( 30H H. -_C:c11_,, ' 8f Orig/3'“ H CH3 ““4on "4H,” CH —C02H or o I} CH -c 6 ‘11 aways/o? ‘0 . \ 3c. SHOW THE EXPECTED PRODUCT OF THE FOLLOWING REACTIONS: (a) , 0 Hr —C;0H '(go’.#* [K _ CH3, :1 CH3 Haul _ 75 C E - ' ,___ .. r. - gown; CH&— 5 --H —-*- "73"0 “54”.: - H 'on. E2 conditions m CHZI— CH2CH3 ——_-- . , CH2: (9’ 3 'OH, 8N2 conditions H 0 CH2 __ CH2: W3 - CH2 1— CH2CH3 _—_—-— 4a. Use the appropriate chemical equations to show why hydroxide' Ion (pKa H20 =16) Is capable of deprotonating- a terminal alkyne (pKa RC-_-CH,25) to only a very small extent. - 6-9 Hz 0 + H20 75} OH + H509 l/(a'fi' Ina/0‘16 @‘7 Rae-H + H o :5 R—c =59 +H?o 0‘5 g; (J‘s?) I ®+0 R-csc -H+0H é R c=60 +1420 K K:é(a:) a: WWW @fo’fmyflm ‘ _? Mo K Mg M : ’0 b. MECHANISM: Draw a reaction energy diagram for the E2 and 5N2 mechanisms of the reaction of methoxide son with ethyl bromide. Show dearly the appropriate transition states and the products. T§(hc3d£tvlé axe/9“!) TS (”£3412 Me {9 charged) <8) 5” “J", I q I, - w __ , OH H' ‘7' h H ' V ' t a (”37,717 +3fa_m11 . m + Er- _. .; z ‘ £0“ Sflzfr°hd' , up a E), MM 5. _ _ Indicate which of the four molecules (1-4) shown below Is chiral and assign the absolute configuration to the chiral molecule (5). Show reasoning ' l (6) Bonus Question: J. M. Tour at al have recently synthesiZed a series of anthropomorphic molecules: the NanoPutians. What would you call molecule 4 In Question 5? Nano ......... with UN Limogwaflm ...
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