Organic Chemistry 1 ACS Questions Final Exam SOLUTION 2024 EDITON AID GRADE A+

Which is the correct hybridization state and geometry for the carbon atom in HCN? sp, linear sp2, trigonal planar sp3, tetrahedral None of the above sp, linear The following structure has been drawn without formal charges. Which statement describes the missing formal charge(s)? This structure has one positive charge and one negative charge. This structure has one positive charge but no negative charges. This structure has one negative charge but no positive charges. This structure has no formal charges. This structure has one positive charge and one negative charge. The indicated σ bond results from the overlap of which orbitals? sp2-sp2 sp-sp3 sp-sp2 sp2-sp3 sp2-sp3 Of the following molecular geometries, which has the largest bond angle? Pyramidal Tetrahedral Trigonal planar Bent Trigonal planar How many σ bonds are in the following compound? 8 9 13 14 13 Which compound has the higher boiling point? Explain briefly. X, because the dipole moments are far apart. Y, because the dipole moments do not fully cancel. Y, because it is less branched. X, because it is more linear. Y, because the dipole moments do not fully cancel. How many hydrogen atoms are in the compound represented by the following bond-line drawing? 5 6 7 8 6 The compound represented by the following bond-line drawing has how many carbon atoms and how many π bonds? C atoms π bonds (a) 10 6 (b) 10 5 (c) 9 6 (d) 9 5 D) 9 5 All of the following are significant resonance structures of the benzyl carbocation, EXCEPT: C Which of the following resonance structures is the most significant contributor to the resonance hybrid? A Which of the following structures exhibits an sp3-hybridized nitrogen atom? D Which is a bond-line drawing of (CH3)2CHCH2OC(CH3)3? C Which of the following has the correct curved arrow(s) placement to show resonance for the given allylic carbocation? C Which of the following anions is resonance delocalized? A The following cation has a total of how many resonance structures? A Which of the following best represents the resonance hybrid of the given anion? D Which of the following does NOT represent a pair of resonance structures? B What is the strongest base that is present after methyl magnesium bromide (CH3MgBr) is treated with water? C Which side of the following equilibrium is favored? The right side. The left side. Depends on temperature. Cannot determine without more information. The right side All of the following are more acidic than water (H2O) EXCEPT: C All of the following are Lewis bases EXCEPT: D Arrange the following compounds in order of increasing acidity, from the weakest acid to the strongest acid. II < I < III II < III < I I < III < II III < II < I II < III < I Which is the stronger acid, HCl or HBr? Explain briefly. HCl is the stronger acid because Cl is more electronegative than Br. HCl is the stronger acid because Cl is smaller than Br. HBr is the stronger acid because Br is less electronegative than Cl. HBr is the stronger acid because Br is larger than Cl. HBr is the stronger acid because Br is larger than Cl. Which of the indicated protons in the given compound is the most acidic? Proton A Proton B Proton C Proton D Proton D Which of the given compounds is more acidic? Briefly explain. X is the stronger acid because the acidic proton is on a more electronegative atom. X is the stronger acid because its conjugate base is stabilized by inductive effects. Y is the stronger acid because its conjugate base is stabilized by resonance. Y is the stronger acid because the acidic proton is stabilized by inductive effects. Y is the stronger acid because its conjugate base is stabilized by resonance. Of the following, which is the strongest base? A All of the following are representations of cis-1,2-dimethylcyclohexane, EXCEPT: D All of the following are representations of 2-methylpentane, EXCEPT: B Which of the following is expected to have the largest heat of combustion? C Which of the following is a constitutional isomer of heptane? D Provide a systematic name for the following compound. 4-isopropylpentane 2-isopropylpentane 5,6-dimethylhexane 2,3-dimethylhexane 2,3-dimethylhexane Which of the following represents the most stable conformation of cis-1,4-dimethylcyclohexane? C Which of the following conformers has one or more gauche interactions? B Which of the following represents the most stable conformation of the given compound? C Which of the following is the correct IUPAC name for the tertbutyl substituent? (1,1-dimethylethyl) (1,1,1-trimethyl) (1-methyl-2-propyl) 2-methyl-2-propyl) (1,1-dimethylethyl) What is the configuration of the chiral center in the following compound? R S Z Depends on T R What is the relationship between the following two compounds? Enantiomers Diastereomers Constitutional isomers Resonance forms Diastereomers Which of these compounds is expected to be optically active at room temperature? D Identify the CONTINUED....