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210 › McGraw-Hill Education 500 MCAT: Organic Chemistry
466. The nitration of benzene is an electrophilic substitution reaction in which 
a nitro group replaces a hydrogen atom. During this reaction, what are the 
initial, intermediate, and final hybridizations of the carbon atom that is 
attacked by the nitro group?
(A) sp2, sp3, sp2
(B) sp2, sp2, sp2
(C) sp2, sp2, sp3
(D) sp3, sp2, sp2
467. The presence of a free radical is necessary for a free radical mechanism. 
Which of the following is a free radical?
(A) NO2
(B) H–
(C) Cl–
(D) Cl2
468. The bond angles in the methyl radical are all 120°. What type of orbital 
contains the unpaired electron?
(A) p
(B) sp2
(C) sp3
(D) s

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