HWeb03 (Chapter 4.1-4.6, 4.15) Lecture 6, Solomons 4.6; 4.15 3.1. What is the IUPAC name of the following compound? [a]. 2-ethyl-3-methylpentane [b]. 4-ethyl-3-methylpentane [c]. 3,4-dimethylhexane [d]. 3,4-dimethyloctane 3.2. What is the IUPAC name of the following compound?? ClBr [a]. 2,6-dimethyl-3-chloro-4-bromoheptane [b]. 4-bromo-3-chloro-2,6-dimethylheptane [c]. 4-bromo-5-chloro-2,6-dimethylheptane [d]. 2,6-dimethyl-4-bromo-5-chloro-heptane 3.3. Which of the following structures represents bicyclo[4.3.3]dodecane? ABCD [a]. A [b]. B [c]. C [d]. DHWeb04 (Chapter 4.7-4.9; 7.18) 4.1. Which of the following statements is true? [a]. the gauche conformations of butane (along the C2-C3 bond) are more stable than the anti conformation [b]. the eclipsed conformations of butane (along the C2-C3 bond) are more stable than the staggered conformations [c]. the three staggered 2,2-dimethylbutane (along the C2-C3 bond) all have the same energy [d]. an eclipsing interaction between the two methyl groups of butane is more destabilizing than a gauche interaction 4.2. How many rings or pi-bonds are there in a molecule with the formula C8H10O? [a]. one [b]. two [c]. three [d]. four 4.3. Which of the following represents the highest energy conformation of butane? CH3H HHCH3HHCH3HHH3CHCH3H HCH3HHA B C DCH3CH3HHHH [a]. A [b]. B [c]. C [d]. DHWeb05 (Chapter 4.10-4.14) 5.1. Which of the following structures has all of its equatorial substituents marked with black circles? 1432 [a]. 1 [b]. 2 [c]. 3 [d]. 4 5.2. Which of the following is the most stable conformation of cis-1-tert-butyl-3-methylcyclohexane? C(CH)3C(CH)3C(CH)3C(CH)3CH3CH3CH3H3C1432 [a]. 1 [b]. 2 [c]. 3 [d]. 4 5.3 Which of the following transformations represents a ring flip? ClCH3ClCH3ClCH3ClCH3ClCH31234ClH3CCH3H3CClCl [a]. 1 [b]. 2 [c]. 3 [d]. 4HWeb06 (Chapter 4.16-4.17; 10.2-10.6) 6.1. What is the reactive intermediate formed upon irradiation of 2-methylpropane and bromine to form 2-bromo-2-methylpropane? [a]. tert-butyl carbanion [b]. tert-butyl radical [c]. tert-butyl carbocation [d]. tert-butyl alcohol 6.2. What is the correct order of stability of radicals (more stable > less stable)? [a]. 3° > 2° > methyl > 1° [b]. 3° > 2° > 1° > methyl [c]. methyl > 1° > 2° > 3° [d]. methyl > 3° > 2° > 1° 6.3 What is the major product formed upon radical bromination of 2-methylpropane? [a]. 1-bromo-2-methylpropane [b]. 2-bromo-1-methylpropane [c]. 2-bromo-2-methylpropane [d].