Summer 2009 Test 1

Summer 2009 Test 1 - Chisholm Kirby 810187861 1111111111111...

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Unformatted text preview: Chisholm, Kirby 810187861 1111111111111 llll|llll|||11l1||1|l11111111 CHEMISTRY 22]] Exam 1 June 17, 2009 Be sure to read each question carefully. Partial credit will be assigned Where appropriate To receive full credit you must answer the question completely. Relax and gOOd luck" 1. X— 1- (12 p18) DTBW structures for (R—OH) that share the formula CsHuO. I You do not need to indicate the Specific bond geometries. 2' snnply prowde each isomer’s general W“ ’ 2. (8 pts) Name all Ofthe highlighted functional groups in the molecule shown below: 3. (8 pts) Complete Ihe Kekule structure (i.e., write multiple bonds, unshared electron pairs, and assignformal charges where appropriate) for the following overall neutral molecule, only o-bond frameworks are shown. H \l/ C H H H \ .. ,. t. H7C\N/§\C/9\C{O H l / \ l H H H o [3 HI M i i4? :53 ] 4. (6 pts) Name the following compounds in the spac‘es provided using TUPAC guidelines: "sprain / " “'5 ‘" h” i“r_'1’*'"’* h w. at;qu e 4_(1 '1_d]me1hy|ethyl)—6—ethyl~3-methyloctane 4-sec-butyI—7-isopropyI-2.5,5-trimethyldecane )1/ 6. (6 p15) Com-en 1116 following condensed Slmclures into skeleial structures in the boxes provided below: (CH3)2CHCHCHCH20020H2CHZCH3 CHSCHQCWOH )CH(C H3)C H2N(C H2CHs)2 7. (4 pls) Convert the following skeletal structure into a line—hon d structure that clearly shows 31] a10ms_ You do not need 10 indicate specific 3-D geometry: CHI-SHOLM, mm; 8. (12 pts) Provide all ofthe appropriate resonance structures l' or the following compounds. You do not need to indicate electron movement to answer this question. Simply draw the appropriate skeletal structures: 9. (6 pts) Number the following compounds in order of increasing C—C bond length between carbons 2 and 3, (l : shortest and 4 = longest). * 2 4 3 4 2 4 2 _ 5 M5 1M5 1 5 1/;--—__ 1 3 [3 Considering the structure indicated with a star above= the Carbon 2 ~— Carbon 3 Sigma (0) bond is formed by the Overlap ofwhat orbital type(s)? Orbital Contributed by Carbon 3 Orbital Contributed by Carbon 2 / 10. (8 pts) Draw a detailed valence orbital sketch of an sp hybridized carbon atom on the template provided below. Include all ofthe necessary orbitals and clearly label each ofthem with the appropriate orbital designation (ex. 5, p, sp3... etc). ]1. (10 p15) Indicate the hybridization and approximate bond angles for each ofihe atoms _ highlighted in the structure below: Hybridization Bond Angles 12. (8 pts) Draw a three—dimensional line-bond structure of3-bromo-l-propanamine (see condensed structure below). Be sure to clearly indicate the appropriate bond geometry of all carbon and 1111ng en atoms using wedng and dashed/straight lines where appropriate. Indicate the polarity ofboth the C-N and the C-Br bonds using a directional arrow as well as partial charge indicators. You do not need to indicate orbital geometry surrounding the bromine atom. BfC H2O HQCHzNHZ 3-br0mo—1-propanamine ‘ £ I i 13. (8 pts) Provide the appropriate product(s) or steaming materiaKs) for the following acid-base reactions: .rzkmwimzuxucttw 7:25.: E.— vLZmF 3:533..— .C—FEme—Cx. 9:.— ..E v11 .._. 9:57;;— n3 2:. 2:. mm .3 . 3 mm . am mm a mm 5 mm m. E . .3 22 E; mm 5 xm Eu .. .5 $2 .. = E E. 1 .3. 3 t m. 33. :5 :3 Eu 9 £5 a. Ea 9, :a. T 5.2 m. :52 n. 52$ 1 «3an w. 5.3: 962m tum mu mEuEEw B. .o<n=.= .5 3:5: ESE E _m>o.anm 9: 5:: Emma we :5, A.m.$ E 8585 9: $550: mow 265m Ewart—E EEO—m B 25:55 F; ESE; ncm mmEm: u_,_mEu_m>m 9F ............................ .1. N.m.$.~m.s. Tm.mem.wT m.m.mem.m—. — m3 2:. 2:. m2. new 2: mm :2 m: 5 am 8 E . an: E3 .25 am: 55 :E T . ., 37$? 272.5. :Emé. $735. $72.3. $72.2. $32.5. 3.7%.: mééé. “4:35. 37%.. .. w.m._:.E.m.~ 7375.2 mm an .E E. E. n... Nu mm .: .. 3 mm 3 E. =._ no mm an: a. ncn S: m. 5&5 SEE: T 3.5— n. mcafln' 22:: $32.3 $22.3 $73.3 75.2.3 73.5.: 72.3.: $75.3 $12.2 . . 72$.” 9 am an me an m". 9.. my 3. 2. .3 Ha :m E to :m .E as. .22 ..n2 hN > mm m c E: n. 2:: EEE m. BE 2 2a n. :35 m. 33,8 1 an: E :5: "15.3 3:: 273 3.7.2 3:2 #9.: 73.3 3:: New: 3.: 3:2 2.: 2.. E an R on mw aw mu mm E 5 m— : m. mm so 5 ._ 8 mi “52 to n > "H F _ am 8 x . 313 T REE m. er. 2 _. “3m 5. n. “5. mm m. :55. n. ace; m. 53.3, m. “3.2 r; rim 2 N. "ES. 1 Q8 2., N_. m m x. w w v m 2a :3 9.6.5 2 m imam.“ M2. 5.5.!“ .., .. . Z Z .i ., . . . . .. - .. . xx. . . I i. 1 . .. m S a m. 7 7 z l U m .328. 5.558 6 995m vim AI cczmim. co :2 8 . = 5.: 7 225.3 N- .§_m_ m- use... 1 .2:— T :2: E05 9.: .o mEsEnc mmmE Em . .v o _ E m: m... m: m? ,3 m; mwmszEmo E EwnEzc mam—2 “202 0 ll LmnEaz 2E0? ,. , , 9.6.6 _ . _ coo NA. n OE co m 3mm; Em mcmme QEoE 92:55“. 625.5 f _ mEEm coszxO UmEcEw I! VI w E.m_. AT $52 2:32 _ E“, m. 9.85% 9.: 5 «58. 28:8 we ...
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Summer 2009 Test 1 - Chisholm Kirby 810187861 1111111111111...

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