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Exercício de Química Sintética e Organica Mista (160)

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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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