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TAMU CHEM 237 - Proposed Final

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Final ReviewChapter 1a. Which one of the Kekulé structures is not consistent with valence rules?31. What type of hybridization is exhibited by carbon in the following substance?: a. sp3 hybridization and 1 lone pair b. sp2 hybridization and l lone pair c. sp hybridization and 1 lone pair d. sp3 hybridization and 2 lone pairs e. sp2 hybridization and 2 lone pairs f. sp hybridization and 2 lone pairs9. Refer to Exhibit 1-2. The carbon atom in urea is:a.sp3 hybridizedb.sp2 hybridizedc. sp hybridizedd. not hybridized10. Refer to Exhibit 1-2. The predicted NH2−C=O bond angle in urea is:a.109.5°b.120°c.180°d. not predictablea. b. c. d. a. sp3 hybridization b. sp2 hybridization c. sp hybridization33. What type of hybridization is exhibited by the nitrogen atom in the following substance and how many lone pairs are present on the nitrogen?:Chapter 21. Give the corresponding letter of the term that best matches the given definition.a. Brønsted-Lowry Acid f. Ionic Bondb. Brønsted-Lowry Base g. Covalent Bondc. Lewis Acid h. Polar-Covalent Bondd. Lewis Base i. Hydrophobice. Electronegativity j. Hydrophilic2. _____ A bond between two atoms differing in electronegativity by 0.5 − 2.3. _____ A term used to describe a "water loving" species.4. _____ A compound that can donate a proton.5. _____ The ability of an atom to attract the shared electrons in a covalent bond.6. _____ A term used to describe a "water fearing" species.7. _____ Any species that donates electrons.8. _____ A bond between two atoms differing in electronegativity by < 0.5.9. _____ A compound that can accept a proton.10. _____ A bond between two atoms differing in electronegativity by > 2.2. 1. _____ Any species that accepts electrons.23. Refer to Exhibit 2-6. The strongest Brønsted-Lowry acid in the equation is ______.26. An acid with a low pKa:a. is a weak acidb. is a strong acidc. has a weak conjugate based. both b and c45. Based on electronegativity values, in which of the following is the bond, represented by —, the most polar? a. H3C—Ib. H3C—Na c. H3C—Cld. H3C—OH46. Which of the following substances has a zero dipole moment? a. CO2 b. Cl2C=CCl2 c. HOCH2CH2OH d. HCl2CCHCl2 e. All have zero dipole moments.48. How many resonance forms can be drawn for the NO3– ion? a. 1 c. 3 e. None, the nitrate ion does not exhibit resonance b. 2 d. 449. Which of the following would represent the strongest acid? a. b. c. d. 50. Which of the following substances would be expected to have the largest pKa? a. b. c. d. 51. Which of the following does not characterize the curved arrow formalism? a. The arrow shows the movement of electrons not atoms. b. The atom at the head of the arrow is the electron pair acceptor. c. The atom at the tail of the arrow is a Lewis acid. d. The species containing the atom at the head of the arrow will have the smaller pKa. e. All of these correctly describe the curved arrow formalism.54. The following is generic depiction of a reaction using the curve arrow formalism.24. Refer to Exhibit 2-6. The strongest Brønsted-Lowry base in the equation is ______.a. Electrons move from C to B. b. Electrons move from B to A. c. In the products, a bond forms between C and B. d. In the products, A would have a positive charge.Which of these statements is not correct for this reaction?Exhibit 2-2Calculate the formal charges on the indicated atoms in each compound below.11. Refer to Exhibit 2-2. The formal charge on phosphorous (A) is ______.12. Refer to Exhibit 2-2. The formal charge on oxygen (B) is ______.13. Refer to Exhibit 2-2. The formal charge on carbon (C) is ______.14. Refer to Exhibit 2-2. The formal charge on oxygen (D) is ______.Chapter 3 10. _____ a. identicalb. constitutional isomersc. neither12. _____ 11. _____35. How many isomeric chloroalkanes have the molecular formula shown below?C4H9Cl36. If the following alkyl group were attached to a cyclohexane ring,the group would be named as: a. butyl b. isobutyl c. sec-butyl d. tert-butyl37. Which of the following alkanes would have the highest boiling point? a. heptane b. 2-methylhexane c. 2,3,-dimethylpentane d. 2,2,3-trimethylbutane e. All have the same molar mass and would have about the same boiling point.21. Refer to Exhibit 3-4. Draw a Newman projection of the gauche conformation of 1,2-dichloroethane. Explain why the majority of the molecules are not in the gauche conformation. a. 2 b. 3 c. 4 d. 533. Which of the following functional groups if bonded to a three-carbon chain would have the largest δ– charge? a. alcohol b. ether c. phosphate d. sulfide34. Which of the following functional groups contains a carbonyl group? a. ketone b. ester c. carboxylic acid d. amide e. All contain a carbonyl group.ANSWER: The gauche conformation is a higher energy state than the conformation due to the torsional strain caused by the close proximity of the two chlorine atoms.30. Arrange the following conformation from lowest to highest energy.31. Explain your energy order from lowest to highest.ANSWER: The lowest energy conformation of those shown is the one staggered conformation. Of the two eclipsed conformations given, the one in which there is one eclipsed interaction (energy cost: 11 kJ/mol) and one eclipsed interaction (energy cost: 6.0kJ/mol) and one eclipsed interaction(energy cost: 4 kJ/mol, for a total energy cost of 11 kJ/mol + 6 kJ/mol + 4 kJ/mol = 21 kJ/mol) will be higher than the one in which there are threeeclipsed interactions (energy cost: 6.0 kJ/mol x 3 = 18 kJ/mol).Chapter 4 a. CN b. OH c. C(CH3)3d. CO2H35. Which of the following would produce the greatest amount of 1,3-diaxial strain when substituted for Cl in the following structure?36. Which of the following can exist as cis-trans isomers? a. cyclohexane d. 1,2-dimethylcyclohexaneb. methylcyclohexane e. both c and d c. 1,1-dimethylcyclohexane f. all of the above37. The following substituents are attached to a cyclohexane ring. Which substituted cyclohexaneis correctly named as a "cyclohexyl alkane"? a. tert-butyl d. octyl b. 2-methylpentyl e. both b and d c. cyclopentyl f. none of the above38. In methylcyclohexane: a. all carbon atoms are sp3 hybridized. b. ring-carbon atoms are sp2 hybridized and the methyl group is sp3 hybridized. c. all bond angles are approximately 120°. d. ring-bond angles are approximately 120° and the ring-methyl bond angle is approximately 109°.39. Which of the following would have the smallest strain energy


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