Final Exam for Organic Chemistry Lab with Answers, Lab Reports of Organic Chemistry

Download Final Exam for Organic Chemistry Lab with Answers and more Lab Reports Organic Chemistry in PDF only on Docsity! Final Exam for Organic II 200pts(Weighted as 300) Name Good luck all round! 1) Identify the class of compounds each of the following molecules belong to (15pts). R O H R O R O R C O H R C O O-H R C O O C O RR C O O-R R CN R C O NR2 C H N O 2) For each of the amides and amines state whether they are primary, secondary or tertiary (4pts). 3) Circle one of the above compounds that is reactive enough to react with neutral water (2pts). 4) Give two characteristic physical or chemical properties of aromatic compounds (4pts). Final Exam for Organic II Page 1 5) Indicate which of the following molecules are aromatic, non-aromatic or anti-aromatic. (Assume all the molecules are planar). (15pts) N + O N N O H3C H3C CH3 CH3 CH3H3C S N + H NO2 NO2 H + 6) Pick one of the above antiaromatic molecules, and use the polygon rule to demonstrate its antiaromaticity. (8pts) Final Exam for Organic II Page 2 9) Give reagents and conditions to accomplish five of the following transformations. (15pts) CH2CH3 CH2CH3 CO2H CO2H CH2-OH CH2-O-CH2 O O H3C Ph Ph H HO Ph H3C Ph CH2CH2CH3 H A CH2CH2CH3 (no marks for A)!!! CH3CH2 HO2C O2N O2N N 2 CH3 CH3 BrO O O Final Exam for Organic II Page 5 10) The addition of (1 equivalent of) HBr to cis-1,2-dimethyl-3,5- cyclohexadiene generates a mixture of products. HBr mixtureH3C H3C Draw the products, predict their approximate ratio, and mechanistically account for the mixture of products. (10pts) Final Exam for Organic II Page 6 11) Circle the stronger base in the following pairs, and in a sentence explain your choice. (6pts) NH2 NH2 F3C NH C O CH3 H3C NH H2 C CF3 (a) (b) O2N 12) Circle the stronger acid in the following pairs, and in a sentence explain your answer. (12pts) H3C C O OH CF3CH2 OH Cl3C C O OH Br3C C O OH H C O OH H3C C O OH (a) (b) (c) (d) CO2H CO2H CN Final Exam for Organic II Page 7 16) Give the mechanism for one of the below conversions (10pts) S S H H 1) BuLi 2) CH3CH2Br 3) H3O +, HgCl2 C CH3CH2 CH2CH3 O or CH3CH2CH2CH2Cl, AlCl3 Final Exam for Organic II Page 10 17) Give the starting material and mechanism for one of the following schemes. (19pts) (a) NH2 Cl2, KOH (b) O H H O Na, NH3 C2H5OH (c) 1) CH3Br, Ph3P 2) BuLi 3) Warm Ph C Ph CH2 H2O Final Exam for Organic II Page 11 *Bonus question* (1pt for within $5k, 2 pts within $1k) What is the base rate 10 month salary (i.e. excluding summer compensation and consultancy, etc) for an assistant chemistry professor at Rutgers? Final Exam for Organic II Page 12 7) Give the products in six of the following reactions, paying attention to regio/stereochemistry where applicable. (18pts) heat . Q NC—==—-cN —————> y cai Cr/ Excess HBr O-CH2CH2CH3,§ ———————> fol en Be Ph ko H \ Bra, HzO KOH Pk oF ——- A 0 a. B Pk 7H Qh BF Excess HI BEA BPE o owt F F CO, HCl O CuCl, AICl3 Oo ne oO __ 7 heat Uy ae A WwW CHs ‘ Bro, FeBr3 Hy NHCOCH, br Nuccu HE 3 Oo Final Exam for Organic II Page 3 8) The below heterocycle contains two Nitrogen atoms, and is 6m Hiickel aromatic. GH N 2 uy The lone pairs on the two Nitrogens play different roles in the aromaticity of the molecule, and consequently one Nitrogen will get protonated before the other. Describe which one gets protonated first, and explain their differing basicity. forts) ay NN umit Wy fr ommadich. 2 alodins to te T sytom abr it A ae & fn al This N dow woe ve tts & etl mar Waste Nithogs Ano ch, 1 \ ” i inl ode Ths is Us Wes wv i? ae A regattr N - oO cvomaticdy Mownic( = Ca Now~ RROMAKC t Ob Mow iw } My Yrcrornatan g Us low N Voinbains wowalesty low N fe mole asic Final Exam for Organic II Page 4 9) Give reagents and conditions to accomplish five of the following transformations. (1 5pts) be om mech Or cr WSO; hak hook =i -O- “CL. OnN HO H O° © Wa cH, Gh br e-7 se eo Heo] oHsoHit Ph Ph x0 CH,CHg ties. an COjH 4 Ole CH3CH; CH,CH3 x0 HO,C CO.H ame RE Ady Oo Br O Cp As A aay ( protucictt HC! (no marks for A)!!! Final Exam for Organic II Page 5 13) Name five of the following compounds in IUPAC acceptable terms. (15pts) Ons gee 00 ® . £ 3 ¢ s % CU oO CY WO Non : S hydaony poatarere Dh Loxsae Eres, e-thony -b-wahyecong hy oe a be rs O é “I AL 0 ey oe a NH L & ° OT a? i Yaoroy Q nae Bar poproat + shi 26d leclan 14) Rank methanal (formaldehyde), propanone and propanal in increasing reactivity with nucleophiles, and explain their differing reactivities. (12pts) oO o t, 0 ct is loss Feackve than Giga" is ess renckive Shan uty a % _ : tors Wx Awe al svbckbods Yockig Me once ate 4 te sloop stan eye codon Calan, low, Me ofall \nos on aDhg sibikhat 05 Yo raha \s \. par acagde Gue i is lode only 4 duo Nabe cabo . Oo ( o Abus we, oS so ives Te aro ve is vate. he wee Mac, fe 3 seluio~ wit oy MN co eso dadvaebe cH: Me \nvomg rodeo . . o Ps ohoxe walu Final @ Clo dtiowes : we yk xam for Organic II Page 8 15) Fill in the blanks for five of the following reactions. (25pts) u a C ? 1) excess Mg Co] » OC — 7 2) excess CO, Br 3) Hs0* OH D Way, S04 NH2 H 2 1) NaNOz, HCI (b) CO her 2fo Oe, Ket 2) H3PO>, heat uae CHzOCHs 9.5 yioy CH OCHs ©) ok _NaOCHs | __? 06) D CH.COH Ney, het CH,CONH, OohcEw 2 P20. r (d) : ele ? (ol 7 u ) CH,CN ObbeBe CH,-Cmph ally CH CH Ph Oyo Ma (e) ? ? ° Ne Oo (ow cl AKO), & (f) {ol 2 SOCIl, OQ 2 H SZ — Final Exam for Organic II Page 9 16) Give the mechanism for one of the below conversions (1 0pts) a 41) BuLi 9 Ss Cy Hoy 2) CH3CH2Br CH3CH7” ~CH2CH3 3) H30*, HgClp or ° CH3CH,CH,CH,Cl, AICI, hn J SW ae | \E Final Exam for Organic II Page 10