University:
Amherst College
Course:
CHEM 221 | Organic Chemistry I
Academic year:

2010
Views:

90

Pages:

10
Author:

Veronica Meyer

DarK Final Exam Chem 22 May 11, 2010 Name Gang Sugder page 1(30) 2 (40) 3 (40) 4(35) 5(35) 6(30) 7(25) 8(35) 9(40) total (300) chk Go ahead and write in this space... NOT. (a) nitrips) y 3- they Sita stereochem where relevan; don't abbreviate groups. (b) N-butyl-m-chloroaniline voz (c) 3-cyclopropoxypropanamide (d) 5-methyl-S-hexenal -N|2 (e) The imine formed by acid- catalyzed reaction of benzaldehyde and isopropyl amine (aka 2-propanamine) 2. (13 points) Write a mechanism to explain the following reaction. Show every step clearly with curved arrows. Two equivalents of methyllithium is required; if only one equivalent is used, all the benzoie acid is recovered after the second step. 001f CHLi (2 equiv) H,O' ,CH, - C; Ph ph pu 7 4 942 01) CH, yolake 97 in See a anim os the sin tende is ear end lions nabl may albreviate proton H.0* 6. (17 points) Starting with either malonic ester or acetoacetic ester, suggest a synthesis of the ketone below. You may use only compounds available in the Chemical Store (catalog attached at the end of this exam). CO, E7 Ph can't attach thes via sur chen! -907 • C/ NAPH casi 7. (18 points) Suggest a synthesis of the amide below, using benzene as the only source of aromatic rings. 9. (17 points) N-methylaniline, Ph- NHCH,, displays the following 'H-decoupled "'C NMR spectra at the temperatures indicated. Only the aromatic region is shown. (a) Briefly explain the difference between the two spectra in terms of the structure of the compound. (b) Assign the peaks in the room temperature spectrum to the aromatic Cs. P Room temp -133 °C 8150 CH, e-rotation last 2 ing Cs beca azure on NMR trouscale CH, e rotation stom 810 artha ts are ver Attent end, them as p upfidel due to vermance pages a-donation y~ 35 10. (15 points) The structures and UV-vis spectra of ß-carotene and cyanidin chloride (an anthocyanine derivative), are shown below. HO ОН| 12. (25 points) Isobenzofulvene's HOMO and LUMO are shown below (top lobes of the p- orbitals only). LUMO HOMO (a) When this compound reacts with a dienophile (we'll use ethylene for simplicity), one of the two products shown is formed. Use Frontier Orbital Theory (i.e. HOMO-LUMO interactions) to decide which product is formed, and circle it. Explain your choice by making some sketches in the space below. H,C=CHz or makes ho HO - LU = inconclusive (b) When the compound reacts with cyclopentadiene, one of the following two products is formed (ignore stereochemistry for this problem). As you did in part a, use frontier orbital theory to decide which product is formed and circle it. Make some sketches to justify your choice.

Chemistry 22 Final Exam Solutions 2010

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