8ASum09FinKey

8ASum09FinKey - I) Nomenclature: (24 points) Give the IUPAC...

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Unformatted text preview: I) Nomenclature: (24 points) Give the IUPAC name for each of the following compounds, or draw the correct structure for the given name. 'CWGW' 3;" CLiMébw" L" “(hum/mi CI OH .. gr B) 2-4,5-dibromo-2-hexene ‘//\‘/\ Br ~I'So§>m§m<\[ m/dopemlmu 0 C) O’ f a, . Y C‘ZCIOPL‘MH' isayompv‘ QM“ Cl 7 x I D) {mm’ §~£€r~évl>vi~1L2£WmCyclaRmrz é 1K 0522323" é’IEPP—ébw’ «zil‘ldypqc/guxé K E) 3,1i'clic1‘l9’0 «52€#7/-2,6»J3Mh\7/Azpinn F) 3 L)PM'WOOC’ It“ 7‘YM-2-L,’ p), 2R,4E-2-bromo-5-eth I-4-octen G) V 6‘ aw H) 5 LHWD’ L1 Jiméfl7’C\/doh€?+~2’e”" a} 2) Vocabulary: (35 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) An 8N2 reaction proceeds with an music’s of stereochemistry, while SNl reactions proceed with 5c m mining; of stereochemistry. B) A nucleophile generally has a full or partial charge and @ accepts electrons. C) Ox1dation of a primary alcohol always I' @I never gives an aldehyde product. D) True False. An alcohol has priority in naming over an alkyne. E) Hydrocarbons contain C and fl . F) A carbon with a triple bond is 52? hybridized and has a ll NPN’ shape. G) lnfiared spectroscopy allows us to look for the presence of different types of lo 0 nd’ M, and does @t allow for exact identification of an unknown. H) Axial I @bsfituants are more stable on a cyclohexane 1) Rings wit 0th substituants on the same side are C. l3 rings. J) SNl and E1 reactions both have a Carboalsdw intermediate. K) 8N2 reaction rates depend on the concentration of M «Hugh. and fo Z £14“th L) A Lewis acid g ggfgl's electrons. M) Electronegativity increases as we go j! and *9 on the periodic table. N) A compound that is dextrorotory rotates plane polarized light I [6 hi and is given a {'1' 2 alpha. 0) Lindlar’s catalyst with an alkene will always give @/ trans alkene and acid by @/ anti mechanism. P) In organic chemistry NMR is used to look at what two types of nuclei? _.‘_H__ and Q) A pair of molecules that have the same atom connections that are mirror images and nonsuperimposable ar enantiome /diastereomers I meso. R) A tertiary alkyl halide does [@wergoga reactions well because of 5353‘; Hindi/Inc“ . S) Mass spectrometry does / oes n involve absorption of microwaves. T) The orbitals on a tetrahedral carbon are 53:3 hybridized orbitals and tend to form / pi / both / neither be . U) The pKa of an amine is generally about 3 ' 20 while the pka of an alcohol is about l; 3) Reactions: (24 pts) Draw the structure of the expected organic product(s) formed in the following reactions. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. Indicate all relevant stereochemistry. @OH HKnot: diofl A) 0H B)\/H/\_§3§EL_____, \+\‘ Br CH3OH cc“: e) \{A m...» r + Y\ Cl (.14: H2, Pd/C CH3 H) —_*—"“‘—“"—’ 4) Mechanism. (22 pts) Show the detailed reaction mechanism including all relevant arrows, intermediates, and transition states for the following reactions. A (Hi/\H/g‘ c| ) \\\“i\/\ \/i\/\ + H20 1/1‘ I z 3.0 \xst‘ 3? Cl ' H . B) ‘}\ L /\\\/ +c| MCI-Sage c: G) 91°“ W, 9 cc! * 2% 2 3.00’Htim3 6‘ /\\/ 4' (>24 H H 5N] Reaction A is a type reaction Reaction B is a 1:: type reaction 5) Short Answers and Comparisons: (66 pts) A) Determine Whether the following molecules are E, Z, R, S, or none of these. (16 pts) N Ii! cu3 CHZOH Br C m F a c} H CH3 0 Br 5 Z R 2 OH CH3 NH2 0 “k31sz “Shove,” \ CH3 OH H 5 I: E___..- B) Look at the following molecules. List two functional groups other than alkanes for each molecule. (12 pts) \ V 2 A= cwugscg‘lB: amlg == etL-en A=0tl< n B= Q\Loho\ C= 4119;” C) Sketch six of the seven possible isomers of the formula (3411100. (12 pts) /\/\0H m ADA No\ JVOH * OH *O/ D) Unknown A has the following IR spectrum. Circle the molecule(s) below that could give this spectrum. (5 pts) 7-"- M - i1 ‘ -' .L 1,. A --I E) Give all the possible monohalogen products of radical halogenation of the given alkane. Calculate the relative abundance of each of the products. (8 pts) Y\ c I2 hv Cl :1 3X1=3 25‘1’8 “(55'5- (9%]:(5 F) Order the following from good leaving groups to poor leaving groups. (6 pts) HO-R Br—R F—R Cl—R CH3-R NHz-R I-R I—R> Be-E > (1M: > F-R> HO-R 7 NH1-R>CK3‘R GoodLG I BadLG G) Look at the following molecules. How many different types of hydrogen would you expect to see in the 1H NMR? What would the multiplicity be on the indicated hydrogen in a 1H NMR (12 pts) A 1 CH3 A»; 3,0 \Aiok Number of H: (a 3 *’ q Multiplicity: g 2- 3 H) Circle the Lewis Bases among the following (6 pts) I) Unknown B gives the following 1H NMR spectrum. Circlet the following molecule(s) could give that spectrum. (5 pts) 3‘4 m 7% m 1” J) Indicate Whether each of the following pairs is enantiomers, diastereomers, meso, or identical. (16 pts) OH HoO A) [1 £1 _ mama Br Br“ '1' 3? B) Hsc-q ABI‘ H3C~g AH mesa H'Q‘CH v:~ Er 3 H CHEr OH 31' 5, 0H \\ 7, c: = . D) (:j’ E:1\ ananhowed Cl K) Look at the following Newman projections (22 pts) CH OH H H H®h “3°CH3 H 3CH3 H30 H "CH3 "86” H H HQ}? H®H H36®H “£91?” H36 H 3 F CH3 H H H H H A B c D E Which have eclipsed configuration? 8 I E I F Which have staggered configuration? A ,C ’ D Which is the highest energy conformer above? 8 Which have anti configuration? A Which is the lowest energy conformer? A Which gauche configuration? C H2 ...
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8ASum09FinKey - I) Nomenclature: (24 points) Give the IUPAC...

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