322as08_e1_key - Chemistry 322aL Name:EZ WW inI‘(Aka i...

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Unformatted text preview: Chemistry 322aL Name :EZ WW inI‘ (Aka i Basic Organic Chemistry February 11, 2008 EXAMINATION 1 be Answer the following questions in the space provided. Please orggpiaeydfi?‘thoughtsand~~ attempt to make your answer as legible as possible. If we cannot read your answer, it cannot be given credit. Please remember that C-C-C -C without hydrogens and “stick” structural representations will be given N0 credit (except for rings only). Page 8 (last page) contains a table of Infrared frequencies of functional groups, and page 9 a periodic table. These pages may detached from the exam for your convenience. I. (20) II. (32) III. (32.) IV. (20) TOTAL (1049 Read each question carefully in its entirety. Chemistry 322aL Examination 1 page 2 February 11, 2008 I. (20 pts) (a) Circle all structures below wherein oxygen has a formal charge of +1. CH3—8: (b) Circle any of the following that are NOT valid Lewis structures (as written, including charge or lack thereof). T 'l CH3—C—H H B . I F. H\O./ § "(+) o o .0 ' I " H (c) Based on VSEPR (valence shell electron pair repulsion) formalism, circle all of the following molecules or ions that would have a trigonal planar geometry about the central atom. (Lone pairs have not been shown; you must decide based on the composition and charge whether any are actually present.) 5 GQ (CH3)3N ["30+ (d) Based on VSEPR formalism, circle all of the following molecules or ions that would have a linear geometry about the central atom. (Lone pairs have not been shown; you must decide based on the composition and charge whether any are actually present.) CH3 chemistry 322aL Examination 1 page 3 February 1], 2008 11. (32 pts) (6) (3) Using the orbital hybridization model 4 of bonding for the hydrocarbon at the right: I :H H ( ) C—C” What is the hybridization of carbon atoms H "7 \ )4 (3) C5 (1) and (2) 5 '3 H / /C=C\4"‘ 2 (5) H C (49993 (3>and(4> 39—3 / \\ /(1) (5) and (6) 3% (2) C\H What is the local geometry about carbon atoms (e. g octahedral, trigonal bipyramidal, etc.) (1)and(2)__l_\fl_fl__ (3)and(4) trlgoual (5)and(6) tam \ledl’di The shortest internuclear distance between two carbon atoms in this molecule is between i and 2 .(Atom numbers) The longest internuclear distance between two adjacent carbon atoms in it molecule is between 5 and a .(Atom numbers) (b) Organic compounds were originally defined as compounds obtained from \ LNMS organisms The modern definition of organic chemistry 18. 1 {J94 W 03 Carbon Campoumdg Constitutional isomers are. Same. malécular Sorwula 2 W Odom Connec‘l‘wu‘iy Stereoisomers are. W l/MlQCulmn Sum/hula saw Cowna+1uu+y 2 WW shapes Chemistry 3222L Examination 1 page 4 February 11, 2008 (c) In one sentence, why does hexane not dissolve freely in water? (The statement “Likes dissolve likes and water is polar while hexane 1s non-polar” simply begs the question.) H mm. W ilel‘blum W4 warm— 2 +9: Walpolewl dipolewaiwl Mazdrogev. bow— wow WW2 want Number the following types of mteractions in the order of their relative strength (based on individual pairs of molecules and or ions, not bulk interactions). 1 is strongest and 4 is weakest. A Charge — charge H j. Induced dipole — induced dipole _3_ Dipole — dipole A Charge — dipole Considering the ordering you assigned just above, in one sentence why does NaCl dissolve in water? l ~ I l M r0 2 locum/«3 We to} film overhEAkLQ/a: (d) The four basic types of organic reaction are udddil'ibh 2) QlllMl‘Vl a‘l‘lofl ngulogjj‘l- g; +5014 4) warm m 3,2ng The process of bond-breaking where each fragment takes away one of the electrons from the H 2 b°”d‘s°a”ed bOVMglasis . 2 :4 The bond- -breaking where one fragment 1s an anion and the other 1s a cation is called” M. An inductive eflect 15. .(in one sentence). POlaY‘lZQ'l'lOM OClQ electron WWW (fin/19123 W) loos/1M Chemistry 322aL Examination 1 page 5 February 11, 2008 III. (324pts) (a) Show that you understand the formalism of resonance theory by showing all of the additional reasonable resonance contributors for each of the following Lewis structures. Partial structures are provided for your convenience. There may be more partial structures than you need. 0 a 00%;“ ea 0 {x //O \‘ / \ //O \ /O 4‘ /S\‘Q) /S\\ /S§ / ' ' HO 0 Ho 0 Ho 0 (b) Which of the following molecules have molecular dipole moments? (yes or no to each) Cl Br F O I I F\C __C/H F\C—C/H \\ —' "'H "'Br H/ — / _ \ S Cl/C \H Br/ C\'B H F \\o ##yflksfikfil Which of the following are Lewis acids and which are Bronsted acids? 0 (ll CfHa’ OH \ OH A LI 0/ CH3/ l\CHa. g ngn Luci s [email protected]_Lui s Chemistry 3222L Examination 1 page 6 February 11, 2008 Number the following cationic molecules in order of decreasing acidity of the indicated hydrogens (l = most acidic, 3 = least acidic). (”rims “L“ «>sz § {7% CV?” QC” 1 _i_ _2_ (c) Specify the main functional group in each molecule below. I? h) CH3 CH3—CH2-CH2-C\NH2 gem @ (OFGWQX AM mm do, m L, o O OH CH3—CH2-CH2—C\O_CH3 0/ \fle’tom QS‘l‘Q r a l Col/\ol (d) Specify whether each fimctional group below is primary, secondary, or tertiary. 33' es 9+3 We 3 CH3-—CH2—CH—C—CH3 CH3—CH2—CH2—CII—CH3 CHg—CHg—CHz-CH—CH3 2° éH3 3° OH 1" Specify whether each amine below is primary, secondary, or tertiary. $H3 ICH3 ”4'12 } CH3—CH2—NH-lC—CH3 CH3—CH2—CH2-N—CH3 CHg—CHz-CHz—CH-CH3 Chemistry 322aL Examination 1 February 11, 2008 page 7 IV. (20 pts) For each of the spectra below, write its letter in the blank under the structure with which it is most consistent. (Fill in only four blanks. Ignore any absorptions marked by X.) FREQUENCY Wu") 4000 no. :20! non 1400 2m 1m 1.. 14m 12M 1.. M m 400 TRANSMITANCE (56) 100 anme 50 upv‘il o w—r— 4000 3000 2000 1.____._____ 1500 1000 500 Fiequency (cm-1| CH3CH2CH2CH2 ©Oi—A : Freqlmcy (cm“) 4000 3000 2000 1000 CH3CH2CH2C: —N 1600 1400 1200 1000 000 600 Transmission 9 i —T .3500 3000 2500 2000 1500 1000 500 Wovenumber (cmd)...
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