Write your name and date on the cover page Do not open exam until instructed to do so

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1 Write your name and date on the cover page Do not open exam until instructed to do so Name: Date: Exam III Practice Exam Chem. 212 Do not open exam until told to do so. Get out your pencil, eraser, and scientific nongraphing calculator. Put everything else under the desk or on the floor. Turn off or silence then stow all electronic devices. You may leave the exam room after turning in your exam. You may not return to the exam room after leaving (until the exam is over). Provide the best answers as requested. You must show work for credit. Label your work should you use the back side of the paper. If you have any questions during the exam, write them on the exam. When told to do so, check that exam has all of its pages. 1 of 12

2 CH2CCHCH CH2CH2CH2 Δ CH2CCH2 CH2CCHC CH2CH2CH2 CH2CH2CH2 + C2 H +, H2 Δ Q) Provide the name for this compound: benzenamine NH2 CH CH2H Mn2, acetone, 25 C CH2CH2CH2CH2C + NH2 CH2CH2CH2CH2CNH Q) Provide the key product of this reaction CH2CN CH2CH2NH2 LiAlH4, (CH2)2 H +, H2 Q) Provide the name for this compound:ch2ch2ch2ch2cch2 ethyl hexanoate CCH2C CCHC Na, H I CH2CH2CH + CH2CHCH CH2K, CH2CH2H, (CH2)2 2 of 12

3 Q) Provide the key product of this reaction: ()2CHCH2CH2CH2CN + [()2CHCH2]2AlH Toluene H +, H2 ()2CHCH2CH2CH2CH CH CH2CH2 1) KMn4, H, Δ 2) H +, H2 H2 S3Na Q)Which one would be expected to have the highest boiling point? A. B. CH2H C. CH2NH2 D. HC E. CH (B) CH2CH2C + [()2CH]2CuLi CH2CH2CCH()2 E CHCH2 Q) Provide the product of this reaction: CH2C + S3H CH2CCHCCH2 Br N2 F CCH2CH2 Na, H CH2CCH2 CH2K, CH2CH2H, (CH2)2 CH2CH2C CH2CH2 H2, Pd, C CH2CH CH2CH2CH CH2CHC CH2CH Q) Provide the product CH2CH2C of this reaction: CCH2 CH2CH2CH CH2K, CH2CH2H, (CH2)2 CH2CH CH2C H +, H2 CH2K, CH2CH2H, (CH2)2 + CH2CHC CH2CH2C CCH2 3 of 12

4 CCH2 Q) Predict the product(s) of this reaction: CH2H + H CH2 + H2 Q) Provide the product(s) of this reaction: CH2C 3CH2CH2CH CH2CH + H Q) Provide the key product of this reaction : CH2CN CCH2CH2 CH2CCH2 H +, H2 CH2MgBr, (CH2)2 H +, H2 Q) Provide a name for this compound: phenol H Q) Which one best describes the geometry around a nitrogen atom in an amine A. linear B. tetrahedral C. trigonal planar D. trigonal bipyramidal E. octahedral (B) Q) Provide the product of this aisen Condensation: 2 CH2C CH2CCHC Q) Predict the product of this reaction 3CH2C C + LiAl[C()3]3H 1) 2) Na, H H +, H2 H +, H2 4 of 12

5 CH 2 H CH2CCHCH2CH2 N-dodecylthiazolium bromide, NaH, H2 HCCH2 Q) Provide the tri-substituted product(s) of this reaction: + Br2 hν CBr3 + 3HBr Q) Rank the acidity of these compounds (most acidic first) N2 2N H 2N H a. A. b > a > c B. c > a > b C. a > c > b D. b > c > a E. c > b > a a > b > c ( N2 b. N2 H c. H PCC Pyridinium chlorochromate PyH +, Cr3 -, CH22 Q) Provide the product(s) of this reaction: CCH2CH2 + CH2H H Q) Provide the product(s) of this reaction: N2 + NH3 + K2C3 + H2 Q) Provide the key product of this reaction: CCH2 + CH2CH2H H2NCN LiAlH4 KH, H2, (CH2)2, 0 C N H 2N Cr3, CH22 NaBH4 NaBH4, CH2H H CH2CN + N H Na2Cr27, H2S4, H2 H3 + 2N H +, H2 LiAlH4, (CH2)2 CH2CH 5 of 12

6 2N CH2CH C + C Na, H H +, H2 CCH2C CH2CH2CH CH2CH2CCCH2CH2 +CH2CH2C Δ + N N + N()2 H +, H2 NN + N()2 NN N()2 + H Q)Which one is the strongest base? A. ()2N B. ()2NH C. NH2 D. NH4 + E. ()3N ( 2N Br Q)Provide the product of this reaction: N2 + NH3 Δ 2N NH2 N2 Q) Provide the key product of this reaction: CH2CH2CNH CH2CH2CN N NaN2, H, H2, 0 C 6 of 12

7 Q) Provide the product(s) of this reaction: C + NH2 CNH + H Q) Provide the product(s) of this reaction: CH2CH2CH2CNH2 CH2CH2CH2NH2 + C2 2, NaH NH2 NaN2, H, H2, 0 C H2P2, H2 + NaH H2, 340 C, 150 atm H +, H2 H Q) Draw the compound from the name: butanoic anhydride CH2CH2CCCH2CH2 Q) Provide the product(s) of this reaction: ()2CHCH2NH2 ()2CHCH2N2 NaN2, H, H2, 0 C Q) Which product does not form from this reaction: NH3 + Br A. NH2 B. ()2NH C. ()3N D. ()4N + Br E. all of the product form (E) (after step 1) + H3C N N H3C (after step 2) H3C NH2 NaN2, H, H2, 0 C H Δ 7 of 12

8 Q) Provide the product(s) of this reaction:c + 2 MgBr 1) ()3CH THF 2) H +, H2 NH2 NaN2, H, H2, 0 C CuCN, KCN, Δ CN Q) Provide the key product of this reaction: CH2CH2CH2CNH2 + [()2CHCH2]2AlH Toluene H+, H2 CH2CH2CH2CH 2N Q) Provide the key product of this reaction: CH2N()2 CH2CH2CH2CH2CH2CH H3C CH2CH2CH2CH2CH CNH2 CH2CH2CH2CH C CH2CH2CH + HCH H3C + ()2NH H+ CH2CH2CH2CH2CH2CCCH2CH2CH2CH2CH2 H3C Pd, P()3, 100 C + KH H CH2CH2CH2CH2CH2C CH2CH2CH2CH2CCCH2CH2CH2CH2 CH2CH2CH2CH2CH2CBr C H H3C NH CH2CH2CH2CCCH2CH2CH2 CH2CH2CH2CH2C CH2CH2CH2CH2CBr CH2CH2CH2C CH2CH2CCCH2CH2 CH2CH2CH2CBr C CH2CCCH2 CH2CH2C + H2 CH2CH2CBr CC H CH2C NH H CH2CBr C CC CBr Acetone 2 H CHCN CH2CN CH2CH CH 2N H CH CH CH2CH CC Q) Provide the key product of this reaction: CH2CH2CH2CH2Br + KCN CH2CH2CH2CH2CH2NH2 H3C H H PyH +, Cr3 -, CH22 C + ()3C + N H + H + HCH2CH2 + Acetonitrile DMF Nitromethane PCC NaBH4 N,N-dimethylformamide N2 H3C Pyridinium chlorochrom Cr3, CH22 CN Na2Cr27, H2S4, H2 HCN()2 H DMS HMPA H3 + H +, H2 ()2S (()2N)3P Hexamethylphosphoric triamide HCN()2 CC LiAlH4 LiAlH4, (C C Q) Rank these carboxylic acid derivatives in the order of decreasing reactivity toward hydrolysis (most reactive first) H C a. CNH2 C C b. CC CNH2c. C C CCC A. b > a > c B. c > a > b CC ( NaBH4, CH 8 of 12

9 C. a > c > b D. b > c > a E. c > b > a (D) Q) Provide the key product of this reaction: CH2CH2CH2CH2CH2C CH2CH2CH2CH2CH2CH2H LiAlH4, (CH2)2 H +, H2 Q) Provide the product(s) of this reaction:()2chch2ch2ch2ch2nh2 ()2CHCH2CH2CHCH2 + ()3N CH 1) Excess I, K2C3, H2 2) Ag2, H2 3) Δ CH CH2 + HI H + CH2I Q) Provide the key product of this reaction: CH2CNH CH2CH2NH LiAlH4, (CH2)2 H +, H2 CH2CH2CH + S2 CH2CH2C Q) Predict the final product of this conjugate addition reaction: + HBr Br H Br H H 9 of 12

10 Q) Provide the key product of this reaction: CH2CH2Br + NaN3 CH2CH2NH2 Acetone LiAlH4 H +, H2 Q) Provide the product(s) of this reaction: CH2CH2CNH2 CH2CH2NH2 + C2 2, NaH H + CH2Br H, H2 CH2 Q) Provide the key product of this reaction CNH+ H2 CH (+ NH2) Q) Predict the product(s) of this reaction: CH2CH2CH2CCH2 + H2S4, 100 C 3CH2CH2CH2CH2CCCH2CH2CH2CH2C CH2CH2CH2CCCH2CH2CH2 3CH2CH2CH2CH2CH CH2CH2CH2CH + CH2H Q) Predict the product(s) of this 4+2 cycloaddition reaction: + H H CH2CH2CH2CH2CH2C + H2 CH2CH2CH2CH2CH2CH 10 of 12

11 CNH LiAlH4, (CH2)2 H +, H2 CH2NH Q) Provide the product(s) of this reaction: C + [()2CHCH2]2AlH Toluene H+, H2 CH 3CH2CH2C H + CH2C H, H2 CCH2 Q) Provide the key product of this reaction: CH2Br + DMF H +, H2 H, H2 CH2NH2 CH2CHCHCH2CHCH2 Δ CHCHCH2CH2CHCH2 CCH2 C + CH2H Q) Provide the name for this compound: CNH 11 of 12

12 N-methylethanamide Q) Which carboxylic acid derivative has the best leaving group? A. amide B. acyl halide C. anhydride D. ester E. acid (B) Q) Provide the product(s) of this reaction: Br H + 3Br2 Br H Br HCCH CH CCH2 NH CHCH2 + NH2 H2, Raney Ni Q) Provide the product(s) of this reaction: H + C2 NaH, H2, pressure H +, H2 CNa CH (after step 1) H (after step 2) H 12 of 12