1. The reaction below shows radical-mediated halogenation of hydrocarbons. Determine whether the net reaction is exo- or endothermic by calculating AH for each step and for the net reaction? (1) H3C-CH3 + F' H,C-CH2 + H-F Bond BDE (kJ/mol) F-F 157 H,C-CH2 (2) F-F H3C-CH,F + F' Cl-CI 243 + Br-Br 193 I-I 151 H-F 569 H-CI 432 Н-Br 366 H-I 299 C=C (x) 272 C-F 481 C-CI 350 C-Br 284 C-I 209 CH;CH2-H 423

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL2: Mass Spectrometry
Section: Chapter Questions
Problem 24CTQ
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Learning Target 10
Criteria for satisfactory score
Calculations must be without errors. The diagram must satisfy all listed conditions.
Tasks
1. The reaction below shows radical-mediated halogenation of hydrocarbons. Determine whether the net reaction is
exo- or endothermic by calculating AH for each step and for the net reaction?
(1)
H3C-CH3
F'
H3C-CH, +
H-F
Bond
BDE (kJ/mol)
F-F
157
H,C-CH2
F-F
H3C-CH,F
F'
Cl-CI
243
+
Br-Br
193
I-I
151
H-F
569
H-CI
432
H-Br
366
H-I
299
C=C (x)
272
C-F
481
C-CI
350
С-Br
284
C-I
209
CH;CH,-H
423
Figure 7: Multi-step reaction sequence
2. Draw the energy diagram for a reaction with the following paramaters:
• The reaction has 2 steps
• The overall reaction is not spontaneous.
• The first step is a slow equilibrium (K = 1).
• The second step is faster than the first step.
Label substrate, product, transition states, and intermediates on your diagram.
REACTION PROGRESS
Figure 8: Reaction energy diagram
FREE ENERGY
Transcribed Image Text:Learning Target 10 Criteria for satisfactory score Calculations must be without errors. The diagram must satisfy all listed conditions. Tasks 1. The reaction below shows radical-mediated halogenation of hydrocarbons. Determine whether the net reaction is exo- or endothermic by calculating AH for each step and for the net reaction? (1) H3C-CH3 F' H3C-CH, + H-F Bond BDE (kJ/mol) F-F 157 H,C-CH2 F-F H3C-CH,F F' Cl-CI 243 + Br-Br 193 I-I 151 H-F 569 H-CI 432 H-Br 366 H-I 299 C=C (x) 272 C-F 481 C-CI 350 С-Br 284 C-I 209 CH;CH,-H 423 Figure 7: Multi-step reaction sequence 2. Draw the energy diagram for a reaction with the following paramaters: • The reaction has 2 steps • The overall reaction is not spontaneous. • The first step is a slow equilibrium (K = 1). • The second step is faster than the first step. Label substrate, product, transition states, and intermediates on your diagram. REACTION PROGRESS Figure 8: Reaction energy diagram FREE ENERGY
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