2005 exam 3-1

2005 exam 3-1 - CHEMISTRY 2211 EXAM 3 NOVEMBER 2 2005 SCORE...

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: CHEMISTRY 2211 EXAM 3 NOVEMBER 2, 2005 . SCORE Be sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! 1 1. (10 points) Use the reaction diagram below to answer the following questions. ' 2. 3. E LH 4. 5. Energy 6. E“ 7. 8. Bonus NAME Reaction Progress Answer the following questions by writing a letter from the diagram. Identify steps using two letters, such as step X to Z. TOTAL .._._‘ This(the'se) step(s) is(are) exergonic. IE +09 This(these) transition state(s) more closely r'esemble(s) the product(s). [3; 15 This(these) transition state(s) more closely resemble(s) the reactant(s). F The reaction intermediate(s) is(are) found here. .C E I Ase cs5 _.....____.+_____......... AHC :th Ebb This(these) step(s) is(are) endergonic. This(these) step(s) is(are) easily reversible. This(these) step(s) is(are) not easily reversible. Overall this reaction is ' ngaggl c. (exergonic or endergonic.) 2 _ 2. (10 points) Draw and name all possible monochlorinated products from the radical chlorination of 2-methylpentane. . CH3 l a 012 CH3CHCH2CH2CH3 "T ' monochlorinated products v 2-methylpentane “‘\/\§/\ Hulm— 2-way! (Metam— z-ohloro -1—mw7l Poll-Wu. 4A lb? (4 l c‘ a whim ~1—I‘1cl—L7 l cl Z'cw - - Ora '1’ methyl P‘V‘h’H-v I l~clnlorp—Lf-Ml—L‘7( Wit-am 3. (16 points) Ammonia reacts with acetyl chloride to give acetamide according to the following equation. Draw curved arrows to represent the flow of electrons in each step. :09 ,- : : :0: C —-—.:-——-§—> C H ' 3 C / ""WNH + —" / + / \ 1-130 Cl H3C C1 3 H30 2 H3C NH2 acetyl choride C} + :61: _ acetamide + NH4+ C1— Follow the flow of electrons indicated by the curved arrows in each of the following reactions, and predict the products that result. Abra H u o H / ' u "LO 0 _______________ /C\ ‘l CH7) 0H3 90¢“ h an,” 3 H co ' [CH3 3 CH3 (0 9 O H l CH3 m . / C_\ + H a0 H H 3 4. (8 points) Vinylcyclopropane reacts with HBr to Yield a rearranged alkyl bromide. >1 H. vinylcyclopropane Draw the structure of the carbocation formed in the initial step of the reaction. M Draw the structure of the rearranged carbocation formed in the second step of the reaction. 69 I . ' l . af‘ . e a Draw the structure of the final product. . 5. (16 points) Consider the molecule drawn immediately below. H3O CHZCHg CH30H2 CH2CHZCH(CH3)2 Is it cis or trans? _ Trans 15 it (E) or (Z)? % . Write its IUPAC name using the (E)/(Z) system. (32) -"l- 5% l-‘S,’7-&i.~u,’rl« \ —3«~oo+m,e.. - 4 Write IUPAC'names for the following alkenes using the (E)/(Z) system . (a5) —3~Isotw (— :1— cad-me. (3E3 - 3—(Q-mlrh7lprbloyl) ~z meme, 6. (10 points) Draw a structural formula for the alkene of molecular formula CsHlo and the necessary reagents that react to give the following products IN THE HIGHEST YIELD. Br 7 - Br ' 2\/ (5% OCH3 ' ——-—-—-——--~—~> M an?) 0H . Br ‘ /\/\ ‘ Her Br )m 5 7. (20 points) Draw the structures of 'the major product from the reaction of 1- . methylcyclopentene with each of the following reagents. ‘ CH3 $0“ /\\\\ 2 1- ' . i 1-methylcyclopentene ’ (Lr I t . SH H . \C ’1.) :74“ “ o“ : CW5 _ 9 (a) 1- Hg(OAc)2,‘H20 (b) Br; in xs H20 4,, 2. NBBH4 ‘ . i gt . £93 ‘ H (c) 012 _._____._¢,__.___ \ t (e) BI‘2 in XS CH3CH20H (f) HBr EH— (g) l. BHg/THF 2- H202, ’OH / H20 ' 6am; 5:011 ‘ AN“ w; I “ ‘ on (11) 1. 0304/pyridine CEO” 3 \ 2. NaHSOg,H20 a,” 0” ,4, n f‘ H 9*: 0H - (i) 1. 03 2. Zn, I'I30+ (i) KMnO4, P130+ 6 l 8. (12 points) Write a COMPLETE, DETAILED, AND STEPWISE mechanism for the following conversion. For full credit you must Show all electron movement! CH3 . OH H20 . ' __.____.—_——+ - CH , CH 3 H+ 3 _ \—»J»@ CH3 L/ t/\ 043 2 Wu: . W I \j® grills-4!? 0W5 “‘3 M0 /\ (3H - \/L “6 O\H K cu f“ H10 ‘5 l CV13 Br + HBr ...
View Full Document

This note was uploaded on 04/16/2011 for the course CHEM 2211 taught by Professor Hubbard during the Spring '07 term at UGA.

Page1 / 6

2005 exam 3-1 - CHEMISTRY 2211 EXAM 3 NOVEMBER 2 2005 SCORE...

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