316Exam1KeyF06

316Exam1KeyF06 - DON'T KEEP les Kev .’ CHEMISTRY 316 —...

Info iconThis preview shows pages 1–6. Sign up to view the full content.

View Full Document Right Arrow Icon
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 6
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: DON'T KEEP les Kev .’ CHEMISTRY 316 — Fall 2006 EXAM I — Thursday, October 19th NAME: 5 E V (last) (first) INSTRUCTIONS: 1. This exam consists of 7 questions. Do the ones you know how to do first, then come back to the others if you have time. 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, avoid even casual glances at other exams!!!!!! -4.76 MAKE SURE YOUR EXAM HAS 7 DIFFERENT PAGES INCLUDING THE COVER THE BACK PAGE IS A PERIODIC TABLE Name: E y 1. Saquinavir (shown below) is a molecule that is being used as an anti-HIV drug. Answer the questions below related to this compound. F >< g”) a) What is the molecular geometry around atom A? 1"" 10/791 [7 I“ "M 3 b) What is the hybridization of the atom indicated B? 3E t, c) What is the HCH bond angle associated with atom C? "’ I a 7' ; d) What is the name of the functional group marked E? I'm; I'/I C e) What is the name of the functional group marked F? a M l f) What is the name of the functional group marked G? 0100 [7 0% g) What is the name of the functional group marked H? a M ’M h) Put a star next to each chiral carbon. i) How many units of unsaturation does this molecule have? / 7' 2. Write the formal charges for the indicated atoms in the molecule shown below. All lone pairs are shown. / f M \Nl/ H \3/ )VV Name: K5 Y Complete the following: a) Arrange the following compounds in order of increasing boiling point: H N OH 3 4 1 2 Lowest bp: 3 < I < 2 < 5/ :Highestbp b) Arrange the C-H bonds associated with the highlighted C for the following compounds in order of increasing bond strength: CH3CH_C_H2 CHngzCHg HCCH 1 2 3 Lowest bond strength: 9— < / < 3 :Highest bond strength c) Circle the type of electromagnetic radiation with the longest wavelength: Infra-red Visible X-ray @ gamma d) Circle the stretching Vibration that would occur at the highest wavenumber: 6-9 C-C C=C C=O C—N e) Circle the approximate wavenuber expected in the IR for a CN triple bond: 3300 cm'1 2800 cm'1 1700 cm'1 1600 cm‘1 f) Circle the compound below that functions only as a H-bond acceptor: CH3OH CH3CHO CHSCHZCHS CHSCOZH g) The region in an IR spectrum to lower energy of ~1500 cm'1 is called the: Fingerpaint region fingerfood region fingerprint regi h) Circle the Newman projection that represents a conformer of A (shown below): H 0H t 3 ) " I CompoundA Name: g L; V Indicate how each of the following pairs of compounds are related. Your only choices are A) resonance forms, B) structural isomers, C) enantiomers, D) none of the above. Note: lone pairs are not shown but formal charges are. ea > mL 1/ b) \qu — HO H H H >—<fl%H It"?! Name: 5 E y Complete each of the following: a) Sketch the hybrid orbitals used in the molecule HZCNH. Show how these orbitals overlap and indicate all sigma and pi bonds. Carefully show the overall shape of the molecule and indicate approximate bond angles. 77 [VGWQ‘ T ,205( / GU 7/ H! 7 my .5.” gm b) Use correct arrow formalism to draw the three best resonance structures for the following compound. Rank them in order of importance. H .0 \". H- \0: 3 0-2 \oc.@ / H 4 *5 l9 A") & e—a (D F H ® / /i k/ c) Complete the acid-base reaction below, then use the table on the front page to help you decide whether the equilibrium lies towards reactants or towards products. 9 NaNH2 + HCCH <-> NG- CCH 7* “#5 3’0er 25/ (:9 LY!" «MBA/(4L3 33 d) Calculate the units of unsaturation for a compound of molecular formula CngNOZ. Draw two compounds that have this formula that are structural isomers of each other. 9/ Units of unsaturation = O 0 J ( I/‘KD H O H2 /\/1 525‘ , , , H 10 e) Draw the line formula for the compound shown below: (CH3)2CCHCOCH2C(CH3)3 >3“ 3,0 t: 0 Name: 6. You are given a compound with molecular formula C6HBO2 and an IR. Your job is to come up with some possibilities for a structure. Let’s do this in parts: IUD 0| 0 lllmhnll Hmlll‘M D I 000 3000 tool 15 IICI 1000 5 DD IRVENUHI E!“ -II a) What are the most significant absorbances in the spectrum above (3 of them)? Give the approximate wavenumber, and the likely Vibration. Wavenumber 1cm'1 1 assignment 1) page”) .. zfooqm" o~H 2) ~ 17,00 cm A C 3) ref-loo (,rthl cjo b) Suggest a reasonable structure for a molecule that fits with your data. a Ho/LK/vé/ «QM Mans/olc 7. Sketch the most stable and least stable chair conformers of the compound shown below. OH l 1-! 0 Ii 1 0 (—3 cis most stable chair least stable chair my ...
View Full Document

Page1 / 6

316Exam1KeyF06 - DON'T KEEP les Kev .’ CHEMISTRY 316 —...

This preview shows document pages 1 - 6. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online