CHE 118 A Fall 08 MT 2 Key

CHE 118 A Fall 08 MT 2 Key - l. Nomenclature: (10 points)...

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Unformatted text preview: l. Nomenclature: (10 points) Give the IUPAC name for each of the following compounds, include R/S or cis/trans stereochemistry where appropriate, or draw the correct structure for the given name. QH 2-2 - 3 :llwl- 2— Fenland A) m 2.2- E-elkvl pmlwx—Z-ol 12,2 12 - \.2 Alhromo cydokemu Br B 0" . ) [QB from; 4,2 v d-bromo CyC’aLlrQI-L r C) cis-2-isopropylcyclohexanol iv?“ 0 OH OH 3,9.dnoromo -2,‘l'h£¥adi0\ D) ‘ 9 3 z of Br Br I 3th -o\ltbromo he “5'2.” -dn'0| E) 3R, 5R—5-ChIoro-3-methylnonane 29“; each .4 Per error “I? mu 9 2. Vocabulary: (26 pts) Fill in the blanks with the appropriate vocabulary word. If two words are given circle the correct one. A) An enantiomer has a ngnsugc im floabhmirror image. B) A racemic mixture contains a g4 “a! Z I'.\ mix of eWin‘ome/S . C) A carbonyl in IR has weak peak at about 3300 / 2950 / 2200/ 70 m". D) A nitrile in IR has a strong/@ peak at about 3300 / 2950 2200 1700 cm'l. E) An SN2 reaction occurs with scrambling @ maintenance of stereochemistry undergoing §g gks'xd; attack by the nucleophile. F) A secondary haloalkane with a poor leaving group and in the presence of a strongly basic nucleophile is more likely to undergo SNl and Ell 8N2 /@ reactions. . G) The conjugate base of a strong acid is generally bad leaving group. H) In genera®l smaller atoms make better nucleophiles. I) A [(3650 compound containsrstereocenters, but is superimposable on its mirror image. J) A molecule that rotates plane polarized light to the left is ‘g3fl2r0‘\'0f¥ [ ( "'3 and generally contains R / S / stereocenters. K) A chiral center must have how many different groups attached? H L) An SNl reaction will occur better with a primary! secondary @ haloalkane because of Slab.) fit-{Mill “VPfldtgi‘lie intermediate. M) The E‘nég rat "i region of the IR (below about 1500 cm") is not easily interpretable, but can be used to match a known compound to an unknown. N) Which two bonds Show up in about the same place in the IR? -CN and C=O / -0H and -CH2- CH2- and C=0. O) A@ alkane / halogen gets priority in nomenclature and gets the ending ’ . P) Which will have the higher boiling point? CH4 / CH3C1 IQH3OH because it has more H 'hQngLS Z D§ Role, . Q) A signal on the right side of an 1H NIVIR is considered to beQ‘iey} / downfield of and®9l less shielded than a signal on the left side of an 1H NMR. \p)’ I answer 3. Reactions: (24 pts) Draw the structure of the expected organic product(s) formed in the following reactions including correct stereochemishjy, if the reaction is racemic indicate this by either drawing both enantiomers or drawing one and writing racemic. Assume all reagents listed are present in excess unless otherwise noted. If no reaction occurs, state ‘No Reaction’. A) D H2 Pd/C NaOH M (2’ E) /\/\| Mo” Walk M ED Credit OTS CI- Cl 4. Mechanism: (8 pts) Show detailed reaction mechanisms for the following reaction. Include the structure of the expected products and appropriate stereochemistry for all steps. Show a reaction coordinate of the relative energies with the intermediates, transition states, products and reactions clearly labeled. ‘ NaOH 5. Short Answers: A) Determine whether the following stereocenters are achiral, R or S. (8 pts) H Ill CH3 ON C \Br *CHzNHz “\COOH kCHa Cl CH3 H OH HOH20 H H0 CHZCH3 K R 5 «Claw—0. B) Draw the fischer projections of the above molecules. (4 pts) Cl g CH3 c\ H u, CI/K\:/ ‘ “(D/Y H CH3 H Gus OH CN 0" °“ A - B W; ‘cm CH3 0H ’M 0H a H Cl H c, . H H n 40 H a.“ ‘4 H3 H H 3 H C) Circle the substrate in each of the following pairs that will have a faster 8N2 reaction. (6 pts) AK vs CI /\/F VS > [Br/\p vs BFAJ\ D) Circle the nucleophile in each of the following pairs that will have a faster 8N2 reaction. (6 pts) A) “OH sto B) NH3VS@ C)vs HF E) Determine if the following paiis of molecules are enantiomers, diastereomers, meso, or identical (8 pts) CH3 Cl ‘ A) Mom—w CH3 "C! OH? OH CI Cl C CI 7 H M Zack ) H ‘ CH3 c: ‘CH L ( l 3 V H H3O H30 H «(5! H CI 5" RI: CH2CH3 ' QH2CH3 D) CthHS “30:9;0' M HsC'g‘C' CI'Q‘CHe cszcH3 CH20H3 F) Circle all of the following molecules that are optically active. (8 pts) ufiknown A according t5 the IR (6 pts) O OH 0 OH (0 P}; ’2 E»- P" can. Cid:ch .4 9“ each add '1 adv» 8 ...
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CHE 118 A Fall 08 MT 2 Key - l. Nomenclature: (10 points)...

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