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B-10. Which of the following most accurately describes the first step in the reaction of hydrogen chloride with 1-butene? B-11. Which of the following best describes the flow of electrons in the acid-catalyzed dimeriza- tion of (CH3)2C?CH2? B-12. Which one of the following compounds gives acetone (CH3)2C?O as one of the products of its ozonolysis? B-13. Addition of HCl to 3,3-dimethyl-1-butene yields two products, one of which has a re- arranged carbon skeleton. Which of the following cations are intermediates in that reaction? � � � � (CH3)3CCHCH2Cl (CH3)3CCHCH3 (CH3)2CC(CH3)2 (CH3)2CCH(CH3)2 g Cl 1 2 3 4 (a) 1, 2 (b) 1, 3 (c) 1, 4 (d ) 2, 3 (e) 2, 4 (a) (b) (c) (d ) (e) C H3C CH3 C CH3 CH3 H2C C CH3 CH3 H2C H3C H3C C CH2 CH3 � (a) (b) C CH3 CH3 H2C H2C H3C C CH3 H3C H3C C CH2 (c) (d) C CH3 CH3 H3C � Cl H Cl H Cl H H Cl � � � � � � � Cl Cl Cl� Cl� H� (a) (b) (c) (d) REACTIONS OF ALKENES: ADDITION REACTIONS 155
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