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CHEM 316 - exam1key

CHEM 316 - exam1key - CHEMISTRY 316 — Fall 2007 EXAM I...

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Unformatted text preview: CHEMISTRY 316 — Fall 2007 EXAM I — Monday, October 8th NAME: K 5 7’ (last) (first) INSTRUCTIONS: 1. This exam consists of 6 questions. 2. If you run out of space working a problem, use the back of that page and indicate on the front that you have done so. 3. Please, do your own work! 'PK—a 45mm" freuenc cm‘1 _—6.36 _flC-H(s ) tri-le (CH3)3COH ___— ___— CH3CH3 ___ MAKE SURE YOUR EXAM HAS 9 DIFFERENT PAGES INCLUDING THE COVER THE BACK PAGE IS A PERIODIC TABLE Name: KL“? 5’ l. a) Answer the questions about the structure shown below. All bonds are shown, but lone pairs are not. Assume that each atom has a formal charge of zero. O I) what is the bond angle around carbon #1? j 90 2) name the functional groups shown: MLL‘IM—B) 13M' M C) 55 star" 3) place [one pairs on all atoms that need them. 4) how many sigma bonds does this molecule have? i 5’ 5) how many pi bonds does this molecule have? i 2 6) what is the hybridization of the nitrogen atom? SE 7) What is the geometry around carbons #2? I i A 6 at” #3? iff and Lana! #4? Mailed/41 b) Show formal charges for the indicated atoms of the following molecules. All unshared electron pairs are shown. @\ .NI _'..;_,__ O AJKNCB c) Now, show formal charges for ALL charged atoms in the molecules below. Again, all unshared electron pairs are shown. 93/” ' u 1"“ c @ Hzc/ \Ez'Ha Hac/"\0. 6 :0H Name: K E Y a) Convert the following condensed formula into the correct line formula. 0 (CH3)3CCOO(CH2)3OCH2CHO ::> )r‘k 0 mo ’ 71’ H O to) Convert the following condensed formula into the correct gsz Dot Structure, then give the correct geometry and hybridization at C#l. Finally, carefully sketch all the atomic orbitals (hybrid and nonhybrid) used in this molecule. Show how these overlap in your drawing, and point out sigma and pi bonds. H2C2CH2 I::> l Geometry aboutClll :9 I lVl Laf- l 5? Hybridization of CH 2:) Sketch: l c) Convert the following condensed formula into the correct structural formula (include lone pairs). OHCCHC(CH3)CH0 Name: K E i a) Rank the following compounds in order of increasing boiling point: he \COH F>=o [>7 HO Lowestbp: D < A < '8 < C. :Highcstbp b) Rank the following compounds in order of increasing melting point: :> E} a o Loweslmp: C «c A < 6 < D :Highestmp c) Rank the following from weakest base to strongest base: we 35’ 15'. ‘i m. b 09 AN? Ace Am; A a c o Weakestbase: i < L < i < _B__: Strongestbase d) Rank the following types of electromagnetic radiation in order of increasing energy: Gamma Radio Infrared Ultraviolet Lowest E: Wm < I‘M < ”V < Gamma. : Highest E e) Circle all polar compounds in the list below: 0 "JV @O .6) f) The) bond indicated in the molecule below is an example of which type of bond? /\)/ ionic @ metallic emotional 3co— Name:_____K_E_:/_____ 4. a) For each pair, circle the correct structure for each of the following: 1) the more polar compound: CHCl3 T H a /H 2) the weaker bond: \CC/ \C I H/ CH\ H _ 3) the more water soluble: /©\/I\ OH 4) absorbs at higher wavenumber: 0 fl H 0/ 5) a resonance form for o'- ) e,_ .9 e e b) Use correct arrow formalism to draw one important resonance form for the following. Indicate (circle) which is the more important resonance structure. (Note: all lone pairs are shown, but you must add any formal charges :NVEc—c—CH3 ('9 4 ”a c) Again, use correct arrow formalism‘to draw two resonance forms of equal or greater importance than the one shown. Again, indicate relative importance of each. (Note: this time, charges are shown, but lone pairs are not. Add these lone pairs) :5:9 69 7' 2 e \N 4—, /'\]¢\4—5 /'\//\ mos+ (Maw Name: ’45 Y An IR spectrum was obtained for each of the following compounds, but unfortunately, the spectra were not labeled. Your job is to determine which IR goes with each compound. Please indicate which is which in the box below. For full credit, you must describe how you arrived at your answers. To do this, discuss what stretching frequencies are present and absent for each (write this in the space provided AND identify these on the actual IR’s). O O /“\/\/ O HO [DD IFIINDIILI IIII“.LI4EI OI U “100 3000 2000 15m] 1000 EEO HHVENUHE ER! -il IUD YR INS“ [TTHNE El '4! 0| a “100 3000 20!“ ”DO 1000 film IHVENUHI ERI -Il 5. (continued) HID I’m" Ifltlll IRJVI is of compound: C Discuss below. flu) speed-mm has 0 Maui( SIVLECA *J’OOW‘.) - (5 no atoll—Luisa 5*“ 01 0"“ . flue/1:54, i’z‘ Marl 5: amp 4!. C. IRAQ is of compound: Discuss below. The main/m has 19an 0+! Qisco-zzocw“), 0-“ (sp’) ~ ziao»soo0m", Maw£ (~I900w"), and! Na csc. WILL. I“ #1qu (:4 Law-pal. 8, IR#3 is of compound: i Discuss below. -( 71414 Wum had C-H (*3) ~ZJOO-Boaocns’ we (MGOOMAL and aka has (:44 of M dawn. (“4 7000““) \ 6. Name: K E Y a) For each of the following. predict whether the reaction is product-favored (right) or reactant-favored (left) at equilibrium: 0 0 right or left? 8 55-0 1) + “CH3 = 1-“ CH“ {Inf 2&- Nfi’e 2) NaOH HOH + b) For the following, choose a base that will effectively deprotonate the molecules shown. Also, show the other product that forms. Br n ME” I m 2) HC=CH + .0“; —‘—_h HC=£§ + C'U" c) Write whether each of the following functions as a H—bond donor, H—bond acceptor. both, or neither: 0 I (G. Ago 2, C... d) The two compounds shown below are examples of polymers. The brackets indicate that everything inside the brackets is repeated in a long chain (n times). These types of materials were invented in the early 1930’s. Of the two below, one turned out to work better for making fabrics than the other, partly because it didn’t melt when washing in hot water. Decide which one it is (circle it), and explain (use drawings to assist in your explanation). You may use the is page if you need more room. 4301151343 ‘10 (J4 ...
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