Exam2PRACTICE

Exam2PRACTICE - Quiz 2 Chem 261 Last Name(PRINT First Name(PRINT(8 pts I Nomenclature Draw the following molecules(show stereochemistry where

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Unformatted text preview: Quiz 2 Chem 261 March 22, 2007 Last Name: (PRINT) First Name: (PRINT) (8 pts) I Nomenclature Draw the following molecules (show stereochemistry where appropriate) 1. 3 — ethyl — 2 —— pentene 2. E — 2 — chloro — 3 — hexene 3. 3 — hexyne 4. allyl chloride (39 pts) 11 Reactions of organic molecules. Indicate the products of the following reactions. > Clearly show stereochemistry for starred (*) questions. 1. + Brz —> / \ + Br2—> 3. /=< + H — Br —> * 4. Br; a CH3OH (large excess) 5. 0/ H20 / sto4 —————=,~ 6' 0% MA 2) H202,‘0H, H20 *7. 0/ 1 H3B—SMe2 2) CH3COOD 8. 12 03 a 0A 2) (CH3)ZS Na / NH3 *9. CH3CH2C '=‘ CCH3 1 1. 110 12. HBr W‘s) M per0x1de (1%) 13. 0 NBS (NBS = N — bromosuccinimide) (12 pts) 111 Mechanisms Show how the following reactions occur by writing detailed, stepwise mechanisms. Show all key intermediates. (4pts) 1. O: + H“ "“ 9 CH3 9" BY; (3pts) 2. MOH ————4 heat (5pts) 3. _ @CH3 + Br; —> QCHZBr+ HBr For this reaction show individual steps (the initiation step, two propagation steps and one possible termination step) Calculate AH for each propagation step. (50: Table :4 30C!) (12 pts) IV Synthesis Using common reagents and any organic compound containing fewer than 4 carbons, show how to carry out the following conversions. Show the product after each reaction, but you do not need to show a full mechanism. From E 1. CH3 5 CH3CH2CH2CH3 ‘1’” 0H 1 2. CH3 — C E C — CH3 w‘ C— C ““H £50 Sicm'usmcr ' H V \ m:— OIH 3. CH3— C E C — CH3 CH3— CH2 — - CH3 (6 pts) V. Deduce the structures of A and B from the ozonolysis products: I)‘ 03 (a A ——-————*9 + a ch—H a) “was § B I) 03 0 fl 5 l 1) (“W35 NV” VI Multiple Choice (8 pts) 1. Classify the product(s) from the following reaction as one of the following: (i) a single enantiomer (ii) a racernic mixture (iii) a meso stereoisomer (iv) a mixture of two diastereomers_ CH3 » (No nu! 4-! 01an prIJWVfl) ‘\ M “£0 I Hi t Pun. R Shun '15 0m" I) 050$ "———‘7 O 3) NaHSDs 9r; ~‘——> (H 3 I) 0507 .4“ ‘—————) H r 7") Pu“- fix shmxsomtr (9pts) 2. Order the following species according to stability (1 = most stable 3 = least stable) (9 G) C9 A. CH3 '3 (“Mac “3 CH3“; G) C. //\/ ‘55 N Vi /\/ C9 6) (9pts) 3. Which reaction below is faster, i or ii? . LH g“: ( b) 3,. l 3 A CH3-?-H —-—————————> CHB-C- + H-fir . I , CH3 C }5 (Li) 5" CH3 1 ("3vcf~H ‘l l‘l‘fr at; B. l /\/ 'l CC —-———-‘> /\/O + 2’." ( LL) /\/ l 3' ' 3 + C. Which reaction gives the higher ratio of P1: P2 (i) or (ii)? w M r (L) A J“ 9’; ———> N3 + /\ P. a ., /\ + a A! Q ———-7 L2. (5 pts) Bonus Treatment of the following deuterium-labeled eyclohexene with NBS results in allylic bromination in which the products show deuterium labeling as indicated. Explain this observation. 3r” (1" C1” + D D 50"., Pledge BOND Dysfoc Mm H—H m F"F 23 _ a—a 53 ‘ Er-6r We H'F [24> H-w. [03' H-fir $9 ><= g CH3-X 3c, Cl‘ECHg“ >< CH _, ( ;)ZCH >< go (Gaga—x 77 O GIL-X 72' \-/ X C~H 8059 - H - Clam/3, qfi 1% - CH(C%)1 QS H" “£th 91 CLQO— OCH? H#oH H" OCH3 E: 70 (:8 as 65 65 81 H— (Em—Q $5 H—Q {o3 MUD/J ENE/(em (QM [M2 36 H? {0.1 ...
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This note was uploaded on 03/21/2008 for the course CHEM 261 taught by Professor Austell during the Spring '08 term at UNC.

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Exam2PRACTICE - Quiz 2 Chem 261 Last Name(PRINT First Name(PRINT(8 pts I Nomenclature Draw the following molecules(show stereochemistry where

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