CHEM 2220 SPRING 2022 EXAM4 May 2,2022 NAME: Key. Student ID: INSTRUCTIONS: (On multiple cholce questions cele the single correct answer, (QUESTIONS: 1.(4 pts) Draw the structure of butyl =. wu 2.(4 pts) Indicate whether the following amine is 1,2° or 32 aN 3 3.(4 pts) Arrange the following compounds in decreasing (highest to lowest) order of boiling point. CHCH,CH;CHNH, —CHYCHN(CH),-—«=«CHSCH,CHNHICH, 1 ul m A.Ibtllst @ bub C.I>bIll D.IlfsIist E.bIbI 4.(4 pts) Which ofthese compounds is expected to have the Iowest boiling point? A. CH.CHACHLCHCHINE B,CHLCHCH.NHCHCH, ©cnaiyvcw, B(CHiCH SCHON .(CH),CCHLNE CL5.(6 ps) Circle the stronger base below: o 8 ws why you selected it Lone ftir on N does wok Pavkdpale in feonanu 6. (4 pts) Fill in the blank with the correct word in each case below: (a) Aldehydes are_be4 vey _ (better or worse) clectrophiles than ketones {(b) The hydrogens that are (c orf) tothe earbonyl group are more acidic, 7.(14 pis) Draw a step-by-step mechanism leading to the formation ofthe final product ‘of the following reaction include all arrows, charges, intermediates and final product) OE ig thy 3 ° Ma P+ hyo + 4 _8. (4 pts) Predict the major product forthe following reaction At am Gin) vv__ Now the stove 9.(4 p18) Pretit the product forthe Dieckmann condensation below. AAA~ at10. pts) Predict the produet ofthe Dieckmann condensation below: ° 07 0 4. NaOCHy i Oo, 2 0 ogo ~ ° ° 7 _ Pn, TVA © B © > i 11. (8 pls) Draw the intermediate and final product of the following conjugate addition. 9 9° °o > Rss BAA 0 | ZR © 4 1k12. (4 pls) The Robinson annulation reaction (conjugate addition followed by an intramolecular aldol condensation and dehydtation) which produces the following molecule as final product Hy Co, uses which ofthe following as starting materials? (The reagents are aqueous NaOH and heat), ovodo* he, ovadag* OS” I 0 ° ° cvstotin, * Ey ° cnonoeny Ww v Al fom Cll Dav BV 5 eno + Often nt Q.13. (8 pts) For the following reaction sequence choose among LV to answer the questions. co 50: SOLE (2) The product after reaction | with eyclopentylamine and acid is: (8) The final product afte reaction 2 with sodium eyanoborohydide i: TL 14.4 pts) Whi he final product below (Note: consider Curtis rearrangement)? Aci Neco He TL + We 6 r a ° Aww AY s v v 15. 4 pts) Identify the final product formed when aniline (CL1.NE) is subjected to the following series of reactions: 1) NaNO, H5$0,,05%C; 2) CuO, Cu(NO%)s, HO A.GHLNM, Rana auton D. Cos, None ofthese cies16. (8 pis) Give structures of A and B below. ‘NCH 17.(8 pls) Give structures of A and B below: CO A: ore a ow 18. (4 pts) Predict the final product forthe following reaction sequence. Ak 1. excess CH! ZAwO.1HO ee ore on Aa AA JE Ut 1 x m w