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Consider the following monobromination reaction, then answer the following questions. Consider the following monobromination reaction, then answer the following questions. a) Give the structures and the IUPAC names for the products. b) Give the common names for the products. c) Calculate ΔH° for the overall reaction using the following data for the indicated bond dissociation energies: d) Calculate the percent yield for each product. (relative rate of abstraction of 3° hydrogen is 1600; 2° is 82; and 1° is 1.) e) Propose a step-by-step mechanism for the major product only. f) Draw a schematic potential energy diagram for the rate-determining step (RDS)only. g) Does the transition state of the RDS resemble more closely the reactants or the products? h) Would the value of the activation energy be different for different alkanes? Explain. i) Would the reaction slow down or speed up if I<sub>2</sub> is used instead of Br<sub>2</sub>? Explain. a) Give the structures and the IUPAC names for the products. b) Give the common names for the products. c) Calculate ΔH° for the overall reaction using the following data for the indicated bond dissociation energies: Consider the following monobromination reaction, then answer the following questions. a) Give the structures and the IUPAC names for the products. b) Give the common names for the products. c) Calculate ΔH° for the overall reaction using the following data for the indicated bond dissociation energies: d) Calculate the percent yield for each product. (relative rate of abstraction of 3° hydrogen is 1600; 2° is 82; and 1° is 1.) e) Propose a step-by-step mechanism for the major product only. f) Draw a schematic potential energy diagram for the rate-determining step (RDS)only. g) Does the transition state of the RDS resemble more closely the reactants or the products? h) Would the value of the activation energy be different for different alkanes? Explain. i) Would the reaction slow down or speed up if I<sub>2</sub> is used instead of Br<sub>2</sub>? Explain. d) Calculate the percent yield for each product. (relative rate of abstraction of 3° hydrogen is 1600; 2° is 82; and 1° is 1.) e) Propose a step-by-step mechanism for the major product only. f) Draw a schematic potential energy diagram for the rate-determining step (RDS)only. g) Does the transition state of the RDS resemble more closely the reactants or the products? h) Would the value of the activation energy be different for different alkanes? Explain. i) Would the reaction slow down or speed up if I2 is used instead of Br2? Explain.

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a) blured image_TB1830_00 b) blured image_TB1830_00 c) ΔH° for 2...

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When (R) -2-bromobutane reacts with Cl2/hv, which of the following is true? When (R) -2-bromobutane reacts with Cl<sub>2</sub>/hv, which of the following is true? I II A) Only I is formed. B) Only II is formed. C) I and II are formed in equal amounts. D) I and II are formed in unequal amounts. E) I and II could never form under these conditions. I II


A) Only I is formed.
B) Only II is formed.
C) I and II are formed in equal amounts.
D) I and II are formed in unequal amounts.
E) I and II could never form under these conditions.

F) None of the above
G) C) and D)

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When petroleum is distilled, the fraction that contains compounds with 5 to 11 carbons is known as ________.


A) natural gas
B) asphalt
C) diesel oil
D) gasoline
E) jet fuel

F) All of the above
G) A) and B)

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When Br ∙ reacts with 1-butene (CH3CH2CH When Br ∙ reacts with 1-butene (CH<sub>3</sub>CH<sub>2</sub>CH CH<sub>2</sub>), the hydrogen atom which is preferentially abstracted is the one which produces a resonance stabilized radical. Draw the major resonance contributing forms of this radical. CH2), the hydrogen atom which is preferentially abstracted is the one which produces a resonance stabilized radical. Draw the major resonance contributing forms of this radical.

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∙ ∙
CH3CHCH...

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Which of the following is true about the halogenation of methane, CH4?


A) The activation energy for F ∙ + CH4 → ∙ CH3 + HF is larger than any other halogen.
B) O2 slows these reactions by inhibiting the termination step.
C) The activation energy for I ∙ + CH4 → ∙ CH3 + HI is relatively small.
D) The reaction must take place in the liquid state.
E) I2 is unreactive because the activation energy for I ∙ + CH4 → ∙ CH3 + HI is relatively large.

F) B) and C)
G) B) and E)

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Which of the following products result from the disproportionation reaction between two propyl radicals? Which of the following products result from the disproportionation reaction between two propyl radicals? A) B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CHCH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>2</sub> <sub> </sub> CHCH<sub>3</sub> E) CH<sub>2</sub> <sub> </sub> C CH<sub>2</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub>


A) Which of the following products result from the disproportionation reaction between two propyl radicals? A) B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CHCH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>2</sub> <sub> </sub> CHCH<sub>3</sub> E) CH<sub>2</sub> <sub> </sub> C CH<sub>2</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub>
B) CH3CH2CH3 + CH3CHCH3
C) CH3CH2CH2CH2CH2CH3
D) CH3CH2CH3 + CH2 Which of the following products result from the disproportionation reaction between two propyl radicals? A) B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CHCH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>2</sub> <sub> </sub> CHCH<sub>3</sub> E) CH<sub>2</sub> <sub> </sub> C CH<sub>2</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> CHCH3
E) CH2 Which of the following products result from the disproportionation reaction between two propyl radicals? A) B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CHCH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>2</sub> <sub> </sub> CHCH<sub>3</sub> E) CH<sub>2</sub> <sub> </sub> C CH<sub>2</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> C Which of the following products result from the disproportionation reaction between two propyl radicals? A) B) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>3</sub>CHCH<sub>3</sub> C) CH<sub>3</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> D) CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> + CH<sub>2</sub> <sub> </sub> CHCH<sub>3</sub> E) CH<sub>2</sub> <sub> </sub> C CH<sub>2</sub> + CH<sub>3</sub>CH<sub>2</sub>CH<sub>3</sub> CH2 + CH3CH2CH3

F) D) and E)
G) C) and E)

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Explain how CFCs are linked to depletion of stratospheric ozone.

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CFCs are persistent in the environment until they encounter ultraviolet light in the stratosphere. This interaction with a UV photon will cleave the C-Cl bond in the CFC and generate a chlorine radical. The chlorine radical reacts with ozone to form chlorine monoxide radical and molecular oxygen. The chlorine monoxide radical then reacts with a molecule of ozone to produce oxygen and to regenerate a chlorine radical. The two steps are the propagating steps in a radical chain reaction whereby a single chlorine radical can destroy about 100,000 ozone molecules.

Give the best product for the reaction. Give the best product for the reaction.

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Provide the major organic product of the following reactions. Provide the major organic product of the following reactions.

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The reaction Br2 + CH3Br → CH2Br2 + HBr was carried out. Which of the following mechanism steps is both productive and relatively likely to occur?


A) Br ∙ + ∙ CH2Br → CH2Br2
B) Br ∙ + ∙ CH3 → CH3Br
C) Br ∙ + Br2 → Br2 + Br ∙
D) Br ∙ + CH3Br → HBr + ∙ CH2Br

E) A) and C)
F) A) and B)

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Which of the following is the most stable radical? Which of the following is the most stable radical? A) I B) II C) III D) IV E) V


A) I
B) II
C) III
D) IV
E) V

F) C) and E)
G) C) and D)

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Rank the following fractions which result from the fractional distillation of petroleum in order of increasing boiling point: asphalt, gasoline, kerosene, natural gas, heating oil.

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natural gas < gasoli...

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Why are alkanes so unreactive?

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They have only stron...

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Show the propagating steps in the addition of HBr to 1-pentene in the presence of peroxide.

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Which of the following does not occur in a propagation step in the free radical bromination of ethane to form bromoethane?


A) a C-H bond breaks
B) a Br-H bond forms
C) a C-Br bond forms
D) a Br-Br bond breaks
E) a C-C bond breaks

F) A) and B)
G) A) and E)

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The reaction Br2 + CH3Br → CH2Br2 + HBr was carried out. Which of the following mechanism steps is productive, but relatively unlikely to occur?


A) Br ∙ + CH3Br → HBr + ∙ CH2Br
B) Br ∙ + ∙ CH2Br → CH2Br2
C) Br ∙ + Br2 → Br2 + Br ∙
D) Br ∙ + ∙ CH3 → CH3Br

E) A) and B)
F) A) and D)

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Give the best product for the reaction. Give the best product for the reaction.

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When (R) -2-chlorobutane reacts with Br2/hv, which of the following is true? When (R) -2-chlorobutane reacts with Br<sub>2</sub>/hv, which of the following is true? A) Only I is formed. B) Only II is formed. C) Both I and II are formed in equal amounts. D) Both I and II are formed in unequal amounts. E) Both I and II could never form under these conditions.


A) Only I is formed.
B) Only II is formed.
C) Both I and II are formed in equal amounts.
D) Both I and II are formed in unequal amounts.
E) Both I and II could never form under these conditions.

F) B) and D)
G) A) and B)

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An alkane with the molecular formula C5H10 forms only one monochlorinated product when heated with Cl2/hv. Give the structure and the IUPAC name for this alkane.

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Identify as initiation, propagation, or termination. Identify as initiation, propagation, or termination. A) initiation = b; propagation = a, c, g; termination = d, e, f B) initiation = c, d, e; propagation = b; termination = a, f C) initiation = b; propagation = c, d, e; termination = a, f D) initiation = b; propagation = a, f; termination = c, d, e E) initiation = a, f; propagation = c, d, e; termination = b


A) initiation = b; propagation = a, c, g; termination = d, e, f
B) initiation = c, d, e; propagation = b; termination = a, f
C) initiation = b; propagation = c, d, e; termination = a, f
D) initiation = b; propagation = a, f; termination = c, d, e
E) initiation = a, f; propagation = c, d, e; termination = b

F) B) and E)
G) A) and D)

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