lOMoARcPSD|40947354 Orgo Final Review Tests 1 Organic Chemistry I (The City College of New York) Scan to open on Studocu Studocu is not sponsored or endorsed by any college or university Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 ORGANIC CHEMISTRY FINAL EXAMINATION REVIEW 1 Formal Charge Questions 1.The formal charge on nitrogen in the compound below is ________. (Sum14) -What is the formal charge on oxygen in the following structure? .. H3C O CH3 CH3 -What is the formal charge on carbon in the following structure? Cl C Cl 2.The formal charge on nitrogen in the compound below is ________. (Spr15) 3.What is the bond angle of C-O-C in CH3-O-CH3? 4. What is the bond angle of H-C-H in H2CO? 5. Give the hybridization, shape, and bond angle for each carbon in CH3CN. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 6. What is the formal charge on each of the nitrogen atoms in the following compound: 7. What are the formal charges on the two nitrogen atoms in the following molecule? -What is the predicted shape, bond angle, and hybridization for CH3+? Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Hybridization 1. Which carbon(s) in the following molecule is (are) sp hybridized? (Sum14) -Predict the hybridization and bond angles of the carbon atoms in the following compounds. _ H 3C C H C N 2. What is the hybridization and bond angles for the atom indicated in the molecules below. 3. What is the hybridization and bond angles on the carbon and nitrogen atoms in the following molecule? Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Net Dipole Moment 1. Which of the following molecules has a net dipole moment of zero? (Sum14) A) B) C) D) E) Identifying Functional Groups 1. What functional group(s) is/are present in the following compound? (Sum14) H O O (a) HO (b) O NHCH3 Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 H N (c) NC 2. Circle and identify the functional groups in the following compound. O COOH O HO O O N H 3. Circle and identify the functional groups in the following compound. 4. Circle and identify the functional groups in the following molecule. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 5. Circle and identify the functional groups in the following molecule. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Resonance 1. Draw the resonance structures for the following compounds and circle the one that contributes most to the resonance hybrid. Why? (Sum14) O (a) HN Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 O (b) 3. (12 pts) Draw the resonance structures for the following compounds and circle the one that contributes most to the resonance hybrid. Why? a) b) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 4. (12 pts) Draw the resonance structures for the following compounds and circle the one that contributes most to the resonance hybrid. Why? a) b) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 5. Draw the resonance structures for the following compounds and circle the one that contributes most to the resonance hybrid. Why? a) (6 pts) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 b) (6 pts) 6. Draw the resonance structures for the following compounds and circle the one that contributes most to the resonance hybrid. Why? a) (6 pts) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 b) (6 pts) 7. Draw the resonance structures for the following compound and circle the one that contributes most to the resonance hybrid. Why? 8. Draw the resonance structures for the following compound and circle the one that contributes most to the resonance hybrid. Why? Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Identify Strong/Weak Base/Acid and High/Low Boiling Point 1. Select the strongest base. (Sum14) A) OHB) RCC C) NH2D) CH2=CHE) CH3CH22. Which of the following is the strongest acid? Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 3. Which of the following is the strongest acid? A) Ethanol B) CH3OCH3 C) CH3—NH—CH3 D) 1-Propyne E) 1-propene 4. Of the following compounds, the one with the highest boiling point is: A) CH3CH3 B) CH3CH2Cl C) CH3CHO D) CH3CH2OH 5. Consider the three isomeric alkanes n-hexane, 2, 3-dimethylbutane, and 2-methylpentane. Which of the following correctly lists these compounds in order of increasing boiling point? A) 2, 3-dimethylbutane < 2-methylpentane < n-hexane B) 2-methylpentane < n-hexane < 2, 3-dimethylbutane C) 2-methylpentane < 2, 3-dimethylbutane < n-hexane D) n-hexane < 2-methylpentane < 2, 3-dimethylbutane E) n-hexane < 2, 3-dimethylbutane < 2-methylpentane 6. Which of the following correctly lists the compounds in order of decreasing acidity? A) HCCH > H2O > NH3 > CH3CH3 B) H2O > NH3 > HCCH > CH3CH3 C) H2O > HCCH > NH3 > CH3CH3 D) CH3CH3 > HCCH > H2O > NH3 E) CH3CH3 > HCCH > NH3 > H2O Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 7. The base species arranged in decreasing order of basicity in the sequence: A) OCH3 > CH3CH2 > NH2 > F NH2 > OCH3 > CH3CH2 > F C) NH2 > CH3CH2 > F > OCH3 D) CH3CH2 > NH2 > OCH3 > F E) F > OCH3 > NH2 > CH3CH2 8. Which is the strongest acid: A) CH3CH2CH2CH2CHFCO2H B) CH3CH2CH2CHClCH2CO2H C) CH3CH2CH2CHFCH2CO2H D) CH3CH2CH2CHICH2CO2H E) CH3CHBrCH2CH2CH2CO2H 9. Of the following compounds, the one with the highest boiling point is: A) CH3CH3 B) CH3CH2Cl C) CH3CHO D) CH3CH2NH2 10.Rank the following compounds in order of increasing boiling points. 11. Rank the following in order of increasing boiling points. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 b) (5 pts) Rank the following in order of increasing bacisity. H2 O c) (5 pts) Rank the following in order of increasing acidity. NH3 CHCl2COOH H2 O CH3COOH 12.Rank the following in order of increasing boiling points. b) (6 pts) Rank the following in order of increasing Basicity. CH3COOHNH2- CH2FCOO- Cl- c) (6 pts) Rank the following in order of increasing acidity. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Naming Compounds 1. The IUPAC name for each of the following compounds is: (Sum14) (a) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 OH (b) (c) (d) HO 2. The IUPAC name for each of the following compounds is: (a) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 (b) (c) (d) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 3. The IUPAC name for each of the following compounds is: (a) (b) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 (c) (d) 4. The IUPAC name for each of the following compounds is: (a) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 (b) (c) (d) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 5. The IUPAC name for each of the following compounds is: (b) (c) (d) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Chair Conformations 1. Draw the two chair conformation of the following compounds, and label the substituents as axial or equatorial. In each case, determine which conformation is more stable. (Sum14) (a) (6 pts) cis-1-ethyl-4-methylcyclohexane. (b) (6 pts) trans-1-tert-butyl-3-methylcyclohexane. 2. Draw the two chair conformation of the following compounds, and label the substituents as axial or equatorial. In each case, determine which conformation is more stable. a) (6 pts) cis-1-ethyl-2-methylcyclohexane. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 b) (6 pts) trans-1-methyl-4-propylcyclohexane. 3. Draw the two chair conformation of the following compounds, and label the substituents as axial or equatorial. In each case, determine which conformation is more stable. a) (6 pts) cis-1-ethyl-4-propylcyclohexane. b) (6 pts) trans-1-methyl-3-propylcyclohexane. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 4. Draw the two chair conformation of the following compounds, and label the substituents as axial or equatorial. In each case, determine which conformation is more stable. a) (6 pts) b) (6 pts) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 5. Draw the two chair conformation of the molecule shown, and label the substituents as axial or equatorial. Determine which conformation is more stable. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Newman Projections 1. Draw Newman projections of the most stable and the least stable conformation of 2,3dimethylpentane viewed through the C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back). (Please indicate which one is more stable) (Sum14) (b) (6pts) Draw the Newman Projections of most stable and least stable conformation of trans-1ethyl-4-methylcyclohexane. (Please indicate which one is more stable). 2. Draw Newman projections of the most stable and the least stable conformation of 2,3dibromobutane viewed through the C-2—C-3 bond (i.e., C-2 in the front, C-3 in the back). (Please indicate which one is more stable) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 3. Draw the Newman Projections of most stable and least stable conformation of trans-1-ethyl3-methylcyclohexane. (Please indicate which one is more stable). 4. Draw the Newman projection of the most stable and least stable conformers of 3-ethyl-2methyl-pentane viewed through the C2—C3 bond (i.e., C-2 in the front, C-3 in the back): (Please indicate which one is more stable) 5. Draw the Newman Projections of most stable and least stable conformation of cis-1-ethyl-4methylcyclohexane. (Please indicate which one is more stable). Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 6. Draw the Newman projection of the most stable and least stable conformers of 2,3,4trimethyl-hexane viewed through the C2—C3 bond (i.e., C-2 in the front, C-3 in the back): (Please indicate which one is more stable) 7. Draw the Newman Projections of most stable and least stable conformation of trans-1-ethyl4-propylcyclohexane. (Please indicate which one is more stable). 8. Draw the Newman projection of the most stable and least stable conformers of 2,3-dimethylhexane viewed through the C2—C3 bond (i.e., C-2 in the front, C-3 in the back): (Please indicate which one is more stable) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 9. Draw Newman projections of the two chair conformations of the molecule shown. Determine which conformation is more stable. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 Fall 2019 Test 1.a) (2 pts) What is the formal charge on the nitrogen atom in the following compound? b) (2 pts) What is the hybridization molecular geometry (shape) at the carbon atom in the following compound? c) (2 pts) The C2—C3 bond in the following compound results from the overlap of which orbitals? d) (3 pts) What is the molecular geometry at the central atom in Cl 2CO? e) (3 pts) Which of the following compounds have trigonal pyramidal molecular geometry? f) (2 pts) Which of the following compounds has a net dipole moment of zero? Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 2. a) (6 pts) Draw the resonance structures for the following compound and circle the one that contributes most to the resonance hybrid. Why? b) (6 pts) Draw the resonance structures for the following compound and circle the one that contributes most to the resonance hybrid. Why? Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 3. a) (6 pts) Rank the following in order of increasing bacisity. NH2- CH3COO- CHF2COO- H2O b) (6 pts) Rank the following in order of increasing acidity. CH3NH2 OH- H2SO4 c) (6 pts) Rank the following in order of increasing boiling points. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 4. a) (6 pts) Draw the two chair conformations of cis-1-(1-methylethyl)-2-methylcyclohexane, and label the substituents as axial or equatorial. Determine which conformation is more stable. b) (6 pts) Draw the two chair conformation of the molecule shown, and label the substituents as axial or equatorial. Determine which conformation is more stable. Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 c) (6 pts) Draw Newman projections of the two chair conformations of cis-1-ethyl-4propylcycohexane. Determine which conformation is more stable. 5. (6 pts) Circle and identify the functional groups in the following molecule. 6. (6 pts) Draw the Newman projection of the most stable and least stable conformers of 2,3,3trimethylpentane viewed through the C2—C3 bond (i.e., C-2 in the front, C-3 in the back): (Please indicate which one is more stable) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 7. Which of the following cycloalkanes has the most angle strain? a) (3 pts) b) (3 pts) Draw the most stable Newman projection for the following compound as viewed down the indicated bond in the conformation shown. 8. (20 pts) The IUPAC name for each of the following compounds is: (a) (b) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com) lOMoARcPSD|40947354 (c) (d) Downloaded by Joel Alex (joelkareelamannilalex@gmail.com)
