Chem 308_Summer 2010_Exam 2h

Chem 308_Summer 2010_Exam 2h - Chemistry 308 H1/H2 Exam 2...

Info iconThis preview shows pages 1–9. 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
Background image of page 7

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

View Full DocumentRight Arrow Icon
Background image of page 8
Background image of page 9
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Chemistry 308 H1/H2 Exam 2 . August 3, 2009 Student Name (PRINT CLEARLY): Student Signature: ' Section Number (H1 before lecture, H2 after lecture): SEAT NUMBER: Instructions PRINT YOUR NAME AND SECTION NUMBER AT THE TOP OF EVERY PAGE. You Will get no score for the pages missing your name. You Will not get a-copy of your exam if the pages are missing your section number. Please fill out ALL of the information requested at the top of this sheet. This exam consists of 5 multiple—choice questions and 15 questions requiring written responses. To answer a multiple—choice question, circle the letter corresponding to your answer. Questions requiring a written response should be answered clearly and legibly and only in the space provided. Please answer all questions within this exam booklet only. At the end of the exam, you must hand in this complete exam booklet. Do not separate any of the sheets in this booklet or remove the staple. Do not hand answers in on extra sheets. The length of the exam, including time allowed to fill in all responses, is 75 min. Exam Form Number: 1 SECTION (H1 or H2) PRINT NAME ‘1. Rank compounds I — IV in order of their rates of reaction with'methylamine (CHSNI-Iz) in pyridine (> means faster than) (2 points)? ' io/ - 13/ I iO/O/NOZ i0 I II 111 IV‘ AI>III>IV>II BIV>IIIV>I>II , CIII>II>IV>I DIII>IV>II>I EII>I>III>IV FIV>I>II>IH 2. Draw the structure of the major organic product of the reaction shown below (3 points). 0 NaOH, EtOH, heat _.__...______.._—> ? 3. Give the reagents and conditions necessary for the synthetic transformation shown below. Number reactions separately, as usual (3 points). ML ? M —————-—-—-—-——————-—--————> CH . / 3 OH _ Q Total points this page (max 8) = PRINT NAME ' ‘ SECTION (H1 or H2) 4. Which one of the compounds given below is the major organic product expected for the reaction shown (2 points)? N O NaBH3CN, CH3OH, o g # o x is» 5. Draw the structure of N~(2—methylpropyl)~4~methylpentana1nide in the space below (2 points). 6. Give the reagents necessary to perform the synthetic transformation shown below. Number the reagents for separate reactions, as usual. Partial credit will be given for incomplete answers, only if intermediate products are indicated (3 points). CH2 o /u\ ? , or V . Total points this page (max 7) : PRINT NAME ' SECTION (H1 or H2) 4 7. Which one of the compounds shown below is expected to have a carbonyl stretch absorbance at ‘ lowest frequency in its IR spectrum (2 points)? 0 o 5 o o o 0 6H 60 dNHQ do A B C I D E 8. Draw the structures of the organic compounds required to synthesize the amine shown below, using a Mannich reaction (3 points). 1. cat. HCl ? ————-———-—-—-—--> - ' 2. NaOH to l a ' N/ neutralize ! 9. Write a detailed mechanism for the reaction shown below. Use curved arrows to indicate all eleCtron movements and indicate all formal charges clearly (3 points). 0 OH ‘ O V OCH3 - cat. HCl, CH3OH ’ -———-——————-—-——-—-» Total points this page (max 8) = PRINT NAME g 1 SECTION (H1 or H2) '10. Which statement is most correct (2 points)? I A Esters are more completely hydrolyzed in aqueous acid than in aqueous base. ‘ B Transesterication can proceed in acidic conditions but not in basic conditions. C Hemiacetals can be converted into aldehydes or ketones in aqueous acid or aqueous base. D Acetals are stable in aqueous acid but not in aqueous base. E Amide hydrolysis is more complete in aqueous base thanin aqueous acid. F Nitrile hydrolysis in aqueous acid produces an amine. 11. Draw the structure of the major organic product of the reaction sequence shown below (3 points). 0 1.[CH3(huCHflLi—78°C ——————-—-—-—-—-———-—-—-—-—-—-—-—-——-—>~ ? 2. CH3—Br 12. Use the axes provided to draw an energy diagram (enthalpic energy versus reaction progress) for the reaction below. Your diagram should correctly indicate the number Of steps, the rate—determining step and the overall enthalpy change (3 points). 0 O ‘ //fl\g a-<DOCH3 .__+____q» '//fl\\ + Chi Cl OCH3 Energy Reaction Progress Total points this page (max 8) : V PRINT NAME ‘ ' _ ' SECTION (H1 or H2) 13. Which reagent(s) and conditions will result in the best product yield in the synthetic transformation [shown below (2 points). ' o o H ? —---------—-————-—-> A PCC,CH2C12 v B H2,Pd-C c H2,Raney nickel D 1. LiAlH4,THF; 2. HC1,HZO E HZNNHZ,KOH, H20, heat F HN03 14. Draw the structures of an ester and a Grignard reagent that could be reacted together to give the alcohol shown below as the major organic product after aqueous acid work—up (3 points) OH . Alcohol product: Ester: Grignard reagent: 15. Give the reagents and conditionsneeded for the following synthetic transformation (2 points). Total points this page (max 7) : PRINT NAME » ‘ SECTION (H1 or H2) - 16. Draw resonance structures explaining the unusual stability of the phthalimide anion shown below (2 points). 17. Draw a Haworth projection showing the cyclic furanose form (a 5—atom ring) of the carbohydrate shown below, which is D—fructose, a ketohexose. Draw the Qt anomer‘ or the [3 anomer (2 points). CHQOH 0 Ho H H ' OH H OH C'HQOH 18. Draw the structure of the organic compound with molecular fonnula-C10H13NO that matches the IR, 13C—NMR and 1H—NMR spectra on the next page (3 points). Total points this page (max 7) = ' [00 5D TE HNSHI T'THHCEI '4! woo . ‘3000 20011 1530 1000 5RD HFWENUNBEN ~Ii ‘3 C;- MML 200 180 160 140 . 120 100 80 60 40- 20 0 SH .2“ 11 10 '9-8 7 8 5 4 :5 2 1 o PRINT NAME SECTION (H1 or H2) 19. Give the reagents and steps showing how an enamine may be used to obtain the synthetic transformation below (2 points). 0 ’ O 20. Draw a detailed mechanism for the reaction shown below. You must show every step, but protonation and deprotonation steps ay be indicated simply as +H+ or —H+, respectively. Use curved arrows to indicate all electron movements, and indicate all formal charges clearly (3 points). 0 O /u\ HCl, H20, heat __.____.___.._____..._.'__> N / . H OH Total points this page (max 5) : ...
View Full Document

This note was uploaded on 01/12/2012 for the course CHEM 2347621 taught by Professor Mr.boikes during the Summer '09 term at Rutgers.

Page1 / 9

Chem 308_Summer 2010_Exam 2h - Chemistry 308 H1/H2 Exam 2...

This preview shows document pages 1 - 9. Sign up to view the full document.

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