Practice Hour Exam 1, Chemistry 2220, Organic Chem Il 1. What splitting pattern is observed for the methyl protons of isobutyleyclopentane? A. Singlet B. Doublet C. Triplet D. Multiplet 2. Which of the following can be used to synthesize a 3-hexanol from propyl lithium? A. (CHy):C=O B.CH\CH,CH=0_—C. CHyCH=0 thylene oxide (epoxide) 3. Predict the major organic product of the reaction sequence shown: CHiMger cts ~ _thO" Excess Ay AA x : 4. Which of the following is the most stable? A. 1,2-Hexadiene B.1,3-Hexadiene —C. 14-Hexadiene —_D. 1,5-Hexadiene 5. Which is the major product of the following reaction?5. Give the transformations and reagents necessary to synthesize the compounds an the left from the compounds on the right. A. D e oe =o § 1) PhCH20H + TsCl, NaH a NaH, CsH,OH sage => dey i Tach, NaH 2) Bu,NI, acetone 3) NaSMe c. OH b= g 1} H2S0, 2)mCPBA 3) HCI, MeQH D. HO ~fo}, aon 1)mCPBA 2) BFy OEt, E \ 2 on > Oa 1) Ma’, then ethylene oxide 2)mCPBA 3) BF,:OEt, Fi ° OH nO athe oH 1) S0.Cl, (or 1 equiv NaH; TsCl) 2) KOH 3) 1 equiv NaH; TsCI 4) NaHSCH4U Unit Test ‘Name: Date: Part A Multiple Choice Alenify the leterof the choice that best completes the sdatement or answers the question 1. Anamine is characterized by what functional group? iS _ i i wl Sh wa! _. os HCH, ‘The correct name for the compound given above is which of the following? oss eco 1b. 4-cyclopropy!-2-ethyl- L-methy benzene ©. po methyl, ethyleychopropylbenzene ve b, 2ethoxy-$-pentanone 4d. ethoxypentanalChemistry 634: Advanced Organic Chemistry — Synthesis and Resetivity Fall 2013, University of Delaware Prof. Donald Watson Problem Set2 Due Boginning of Class 9/17/13 ‘You may work in groups, unless otherwise noted, No not ty to ft answers on these pages. use separate paper 1) Order tne folowing sets (1 being greatest) and explain why ost electopha 16] Most ais (H:0}, provide pka's foreach orate eat Most acct (ONSO), provide pss for each I E t ©) Longest expected C=0 bond length, 2) Predict the products of the following reactions and provide a complete me a” aot" lo eg,FINAL EXAMINATION -- MAY, 2001 -- ORGANIC CHEMISTRY II, CHEM 2220 -- °A* 1, Whatis the structure of the compound having the formula CigH14 and the following proton NMR spectrum data’? 57.1 ppm, multiplet, 4 H 328 pom sept. 1H 3 ppm, singlet, 3H ppm, doublet, 6 H Which of the following pathways is the BEST for the synthesis of 2-butanol from ethane? a, LCHCH,Cubi Ch KOH, light” heat Cl (CH,CH),CuLi Cl, KOH light light heat " cl, Mg. CH,COCH, _H,0 Tight” “other ether = cl, Mg CH,CHO H,0* = — light ether ether B. 3. Which of the following functional groups is present in all polypeptides? A. Alcohol B. Carboxylic acid C. Amine D. AmideCHE 232 Organic Chemistry Exam Ila April 2,2012 page 2. Score Z 4. Draw structures to fit the following descriptions: O ch Sei t ik RA } (a) the hydrazone that forms when hydrazine is ite ais heated with cyclopentanone Hf “ a (b) theimine from cyclohexylamine and 2-heptanone Ci wa a. a eA a SS OA (0) the conjugated enol form of a cyclopentane-1,2-dione. > i ae . we. trot omevs. ccs she flares structures are unstable, Redraw the m nr able a ie will Be formed: (a) ae peut 3 nee Oe ce) a ow ae Lc ann 6. Draw the mechanism for the acid-catalyzed hydrolysis of the acetal, 1 dimethoxypropane, (CH3CH2CH(OCH3)2 to form propanal and methanol {Hints: steps include; 1) protonation, 2) loss of 14 ‘methanol, 3) addition of water, 4) proton transfer 5) loss of 2% methanol, and 6) loss ofthe proton to give propanal} ow re Ai ae > 2, for wee 7 7. Draw structures for the starting material, reagents or products missing from the following reactions, (@) _Ave/ + AS sal RON by Acecy Seer» ee NOE LOg y cite. Koes < (ey OY YY seiee, ae wes L 4 \ oO aren Ron [acl Lo, (Ad) Xe Salts ALG ot cuts = 0 ie) aORGANIC CHEMISTRY FINAL 2020/2021 FALL Please have this statement below in your submissions: The homework/project assignment that has been submitted by myself is solely my own work and | did not get any aid from other people Name: 1+ Which of these substances contain both covalent and ionic bonds? Explain your answer 2-Which compound(s) contain(s) tertiary carbon atom(s) ? Show tertiary carbons on molecules, <, ms Le 1 3-What is/are the product(s) of the following acid-base mechanism? no f of 4- write down IUPAC na nm me for 5- If the rate of reaction of [0.1 M] sodium cyanide with [0.1 M] 2-bromo-2-methylpropane is 1.2 x 10° M/s, what would be the effect on the overall rate if the concentration of sodium cyanide is increased to [0.2 M] and the concentration of the alkyl bromide is decreased to [0.05M]? (S_1 reaction)erometric configurationsPractice Final Exam, Chemistry 2210, Organic Chem I 1, What is the hybridization of the indicated atom in the following molecule? .— A. sp B. sp* Cc. sp D. not hybridized 2. Name the functional groups in the following molecule (in order from left to right). ° ° ew A A. Secondary alcohol, ketone, secondary amine, ether B, Primary alcohol, ketone, secondary amine, ester C. Secondary alcohol, amide, ketone, ether D. Primary alcohol, amide, ester 3. Which of the following is the strongest acid? OH ° 41)1 equiv. HBr ea 3) 2) KO-Bul-BuOH 3) Oy, CHCl KOtBu a ‘or gives anti- 4)Zn Zaitzev elim. 1) Bra 2) NaOH or NaH 3) NaCN at 4) CN anton * * Br Sia Ji. + > Ko 54 3 a, S-ring forms faster than 6-ring +2. d. % a 5) enlye? ozonolysis product oO” “OH Br (Dy Pd Et ——_> —_ 6) CrOy, pyr. HCI IH —_—> or (pec) Ho K,01,0;. #0" Tones ReagentChem 331 Name _ key Fall 2006 Homework #10 due: 10am, Monday, November 27th 1. (0 points) Deduce the stracture of B, PC NMR: ‘HNMR: and fibin the missing Teagen!s. CoHiOr 935.40) 138.5, 6H 267.12) 1.21.5, m, 4H 28.6,(2) 18-21, m, 4H on Ht/-H,0 a oO HH 79.8,d(2) 3.27, m, 2H Ae Oe oN 2. (10 points) Draw an arrow-pushing mechanism for the following transformation: B c de 7 Se H Cm ete” 3, Outline a synthetic route to D, Show all reagents. You may usc any starting material that incorporates three or fewer carbons in the final product. Absolute configaration does not matter, but ‘you must show how to control relative con fign ration, ont oh A A ° ° ° oO KOH OH —_K,CO, % 1BUOK CR Sn 1 DCHE 232 Organic Chemistry Exam Ila April 2,2012 page 2. Score Z 4. Draw structures to fit the following descriptions: O ch Sei t ik RA } (a) the hydrazone that forms when hydrazine is ite ais heated with cyclopentanone Hf “ a (b) theimine from cyclohexylamine and 2-heptanone Ci wa a. a eA a SS OA (0) the conjugated enol form of a cyclopentane-1,2-dione. > i ae . we. trot omevs. ccs she flares structures are unstable, Redraw the m nr able a ie will Be formed: (a) ae peut 3 nee Oe ce) a ow ae Lc ann 6. Draw the mechanism for the acid-catalyzed hydrolysis of the acetal, 1 dimethoxypropane, (CH3CH2CH(OCH3)2 to form propanal and methanol {Hints: steps include; 1) protonation, 2) loss of 14 ‘methanol, 3) addition of water, 4) proton transfer 5) loss of 2% methanol, and 6) loss ofthe proton to give propanal} ow re Ai ae > 2, for wee 7 7. Draw structures for the starting material, reagents or products missing from the following reactions, (@) _Ave/ + AS sal RON by Acecy Seer» ee NOE LOg y cite. Koes < (ey OY YY seiee, ae wes L 4 \ oO aren Ron [acl Lo, (Ad) Xe Salts ALG ot cuts = 0 ie) aSolution to Advanced Problems in Organic Chemistry Part 1 upto Page 137 Alkenes by MS Chouhan Vibrant Academy Kota for IIT JEE Main Advanced Chemistry Olympiad Balaji Ld, | me 14, (©) CH, HSS, CH, —C—ONa + CO, (A) on! Dis, ond eat, 7 2 oO isan ie ato noe, DE, — £8 (wmabiey HH ‘gar Pa g nb eo bitte OO, * Ce, Is CH, on 17. (A) All reactions are between Girgnard reagent and the reagents having ‘Hor ‘D* :. all are acid-base reactions. Solution to Advanced Problems in Organic Chemistry Part 1 upto Page 137 Alkenes by M$ Chouhan Vibrant Academy Kota for IIT JEE Main Advanced Chemistry Olympiad Balaji(A) condemation (B) debydration ic dehydrorylation (D) reduction 52. Which compound is most sobuble in water? wo ~e J Boa. ‘83. What is the correct formula (A) CH. (8) GH, (€) GH: (BD) CHe ‘84. Which combination of the reactants results in the formation of a hemiacetal? (A) aldehyde and ketone under acidic conditions ® aldehyde and amine under acidic conditions (C) aldehyde and alcoho! under acidic conditions © aldehyde and aldehyde under acidic conditions 85. Which type of molecale will give a positive resut with Tolleas’ reagent, an oxidizing agent? (a) sieht (B) carboxylic acid @) bene34. Provide the product for the following reaction (2 points) \ I NIL Nhy KOH YS A) }-methythexane B) 3-1 C) 4-methyl-2-hexene D) }-methy!- E) d-methyl: yyl-4-hexanol hexene Thenene 3. Which compound is a hemiacetal? (1 point) Cl Ole re ML IV ay B Il © m D) IV E) Allof the above 36. Which reagent(s) eould NOT be used to carry out the following transformation? (2 points) 9 es A) Znitig), HCI? D) NH:NHYKOH/heat B) LiAlH. Ey all of these are equally useful ©) HSCH:CHSH, BF;; then Raney Ni (Hi) Predict the product, when cyclopentancearbaldehyde reacts with phenylhydrazine in present catalyst. (2 points) 38. Predict the product for the following reaction sequence. (2 points) : a ceePractice Hour Exam 2, Chemistry 2220, Organic Chemistry Il 1, How many different resonance structures can you draw for the eyclopentadienyl carbocation? AS B.4 C3 D.2 2. Which of the following hydrogens is MOST acidic? HOW H H # H ~~ Oo HOW B. 6G D. 3. Which of the following will give no reaction? i AIC, - NO, + CH,CH,CH,-Cl ——» FeBr; B. HAC OH + Bry ———> Br, dil. HO, c SO;H ————> AICI, D. Hyco. + (CH),;CHCOCL ——>Organic Chemistry 2536 Name Key Exam 1 Februnry 17, 2011 Student # Honor Code Pledges “I have not given or received assistance with this examination” Signature L. Which of the following compound(s) is/are aromatic? List all correct answers (4 pis) 2. Where in an JR spectrum would you find a strong CO peak from an aldehyde, ketone, amide, or ester’? (4 pts) y B, 1600 -1850 cm" B ©, 1500-1950 em? Answer, L__D. 1500-1850 om | ‘A. 1600-1950 cm” 3. Write the major organie product or produets of the reaction shown below. Major products are those formed in 5% yield or greater (4 pts): Thies, & Hos, H,804 Shoo, | | J 4, Jn the blanks below cach compound, label if as activated (A) or deactivated (D) compared with benzene to electrophilic aromatic substitution. In addition, state whether the compound will Girect the electrophile to the ortite/para positions (o/p) or to the meta position (mn). (4 pts) Ox_-0, ‘CHs Br O a a m OP NGChem 14D, Summer 02 KEY Exam I, page | Last Name 1. PRODUCTS: Draw the structure of the MAJOR product for each reaction including STEREOCHEMISTRY. When applicable, specify whether a reaction gives a pair of enationmers or diastereomers. A. (8 pls) 9 H,st att + enant. You D.(8 pts) NaN, DMSOName: GMU G#: CHEM 314-C02 Final Exam Organic Chemistry IT ‘Summer 2009 ‘Choose the best possible answer: 1. Provide the missing series of reagents that would make the following transformation. 9 oo ? 5 ° Ot om Ke uns Ae tenon no 4 ny OHO) rc, oc ° lg, cHscoooH a 2. Provide the major product for the following transformation. aor oo or 3. Provide the major product for the following transformation 6-hydroxy hex ig SO See y roma is —NOOH CG ~~ 4. Provide the major product for the following transformation JA, Fae UL SUL ole ScHcHonnsiyo" ~,