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# Exam 1 Chemistry 2401 February 9, 2007 (18) I. Draw structural formulas for the following (show nonbonded electron pairs). A. An alkene with a formula of C5H10 B. An alcohol with a formula of C4H10O C. An ether with a formula of C5H10O D. A secondary amine with a formula of C4H11N E. An ester with a formula of C6H12O F. An amide with a formula of C5H11NO (10) II. Draw Lewis structural formulas for five isomers of molecular formula, C3H6O. (9) III. Draw one other resonance structure for each of the following. Dont forget formal charges and nonbonded electron pairs. O A. CH3 C CH CH3 CH2 B. CH3 C. CH3 O C CH C CH3 (12) IV. Show how p orbitals interact to produce the pi bonds in each of the following. I have provided a framework for you to start with. H A. CH3 C N H H CH3 C N H H B. CH2 C O H C C O H C. The real ion represented by the resonance structures below H [CH 2 CH CH2 CH2 CH CH2 ] H C C C H H (15) V. In each of the following you should circle the example that has the largest value for the characteristic indicated and underline the example that has the value smallest for that characteristic. A. Bond dissociation energy for the C H bond. H H C C H H C H C H H H C H H C H H B. Strength as an acid H H C C H H C H C H H H C H H C H H C. Most important resonance structure O C NH CH3 O C NH CH3 O C NH CH3 CH3CH2 CH3CH2 CH3CH2 D. Value of pKa: E. Bond length: HCl HBr HI CH2 CH CH2 CH3 (15) VI. Explain each of the following in terms of the structures of the molecules involved. Pictures may be appropriate as well as words. A. Why the boiling point of n-hexane is higher than for 2,3-dimethylbutane. CH3CH2CH2CH2CH2CH3 n-hexane CH3 CH3 CH CH CH3 CH3 2,3-dimethylbutane B. Why acrylic acid is a strong...