Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Chapter 14.2, Problem 4P
Interpretation Introduction
Interpretation: The explanation corresponding to the given statement that
Concept introduction: According to Hammond’s postulate, the structure of transition state resembles with the structure of compound that has energy near to it.
The formation of carbocation as an intermediate takes place in
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Two useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCI) and chloroethane
(CH;CH;CI). Vinyl chloride is the starting material used to prepare poly (vinyl chloride), a plastic used in
insulation, pipes, and bottles. Chloroethane (ethyl chloride) is a local anesthetic. Why is the C- Cl bond of
vinyl chloride stronger than the C– CIl bond in chloroethane.
Appendix 2: Table of Average Bond Energies (kJ mol·!)
Single Bonds
H
C N
F
Si
P
Br
I
436
413
391
463
565
328
322
347
432
366
299
346
305
358
485
272
339
285
213
N
163
201
283
192
146
452
335
218
201
201
F
155
565
490
284
253
249
278
Si
222
293
381
310
234
P
201
326
184
226
255
242
216
208
Br
193
175
151
Multiple Bonds
N=N
418
C=C
610
N=N
945
C=C
835
C=N
615
C=0
745
C=N
887
C=0
1046
0=0 (in 02)
498
Estimate the heat released when 1-butene(CH3CH2CHCH2) reacts with bromine to give CH3CH2CHBrCH2Br. Bond enthalpies are CH : 412 kJ/mol; CC : 348 kJ/mol;CC : 612 kJ/mol; CBr : 276 kJ/mol;BrBr : 193 kJ/mol.
1.317 kJ/mol
2.507 kJ/mol
3.95 kJ/mol
4.288 kJ/mol
5.181 kJ/mol
Chapter 14 Solutions
Organic Chemistry (6th Edition)
Ch. 14.1 - Prob. 2PCh. 14.2 - Problem 16.3 Draw a second resonance structure for...Ch. 14.2 - Prob. 4PCh. 14.2 - Problem 16.5 Farnesyl diphosphate is synthesized...Ch. 14.3 - Prob. 6PCh. 14.4 - Prob. 7PCh. 14.4 - Prob. 8PCh. 14.8 - Problem 16.12 Using hybridization, predict how the...Ch. 14.8 - Problem 16.13 Use resonance theory to explain why...Ch. 14.9 - Prob. 15P
Ch. 14.9 - Prob. 16PCh. 14.10 - Problem 16.17 Draw a stepwise mechanism for the...Ch. 14.11 - Prob. 19PCh. 14.12 - Problem 16.19 Draw the product formed when each...Ch. 14 - Prob. 32PCh. 14 - 16.31 Which of the following systems are...Ch. 14 - 16.32 Draw all reasonable resonance structures for...Ch. 14 - Prob. 35PCh. 14 - 16.35 Explain why the cyclopentadienide anion A...Ch. 14 - Prob. 38PCh. 14 - 16.37 Draw the structure of each compound.
a. in...Ch. 14 - 16.41 Draw the products formed when each compound...Ch. 14 - Prob. 44PCh. 14 - 16.43 Treatment of alkenes A and B with gives the...Ch. 14 - 16.44 Draw a stepwise mechanism for the following...Ch. 14 - Prob. 47PCh. 14 - 16.57 A transannular Diels–Alder reaction is an...Ch. 14 - Draw a stepwise mechanism for the following...Ch. 14 - Prob. 62PCh. 14 - Prob. 63PCh. 14 - Prob. 64PCh. 14 - Prob. 65PCh. 14 - 16.65 The treatment of isoprene with one...
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- Estimate the heat released when ethene(CH2=CH2) reacts with HBr to giveCH3CH2Br. Bond enthalpies areC-H : 412 kJ/mol; C-C : 348 kJ/mol;C=C : 612 kJ/mol; C-Br : 276 kJ/mol;Br-Br : 193 kJ/mol; H-Br : 366 kJ/mol. Choose the correct answer:1. 1036 kJ/mol2. 58 kJ/mol3. 424 kJ/mol4. 200 kJ/mol5. 470 kJ/molarrow_forward7 The pentadienyl radical, H2C“CH¬CH“CH¬CH2#, has its unpaired electron delocalized over three carbon atoms.(a) Use resonance forms to show which three carbon atoms bear the unpaired electron.arrow_forwardTwo useful organic compounds that contain Cl atoms are vinyl chloride (CH2 = CHCl) and chloroethane (CH3CH2Cl). Vinyl chloride is the starting material used to prepare poly(vinyl chloride), a plastic used in insulation, pipes, and bottles.Chloroethane (ethyl chloride) is a tica roman local anesthetic. Why is the C–Cl bond of vinyl chloride stronger than the C–Cl bond in chloroethane ?arrow_forward
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