489 11/ (CH3)2 HCH3 HCH2CH3 HCH(CH3)2 H-C(CH3)3 435 104 (CH3)2CH-Br 285 68 410 98 Bonds to methyl (CH3)2CH- 222 53 397 95 CH3-H 435 104 (CH3)2CH-OH 381 91 381 91 CH3-F 456 109 473 113 CH3-CI 351 84 CH3 H- CH3 Br 70 H3C-C-x 293 CH3 234 56 CH3 356 85 CH3-OH 381 91 (CH3)3C-H 381 91 (CH3)3C-F 444 106 H 464 111 (CH3)3C-CI 331 79 H3C-C-x (CH3);C-Br 272 65 364 87 (CH3)3C-I 209 50 H-F 569 136 CH3CH2-H 410 98 (CH3)3C-OH 381 91 H-CI 431 103 CH;CH2-F 448 107 H-Br 368 88 CH;CH2-CI 339 81 X-X bonds 297 71 CH;CH2-Br 285 68 159 38

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.3: Stability Of Cycloalkanes: Ring Strain
Problem 8P: Each H↔H eclipsing interaction in ethane costs about 4.0 kJ/mol. How many such interactions are...
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TABLE 6.1
BOND DISSOCIATION ENERGIES (AHº) OF COMMON BONDS
KJ/MOL KCAL/MOL
KJ/MOL KCAL/MOL
KJ/MOL KCAL/MOL
Bonds to H
H2C=CH-CH3
385
92
(CH3)2CH-F
444
106
H-H
435
104
HC=C-CH3
489
117
(CH3)2CH-C
335
80
H-CH3
435
104
(CH3)½CH-Br
285
68
H-CH2CH3
410
98
Bonds to methyl
(CH3)2CH-
222
53
H-CH(CH3)2
397
95
CH3-H
435
104
(CH3)2CH-OH
381
91
H-C(CH3)3
381
91
CH;-F
456
109
473
113
CH3-CI
351
84
CH3
H3C-C-x
CH3-Br
293
70
CH3H
234
56
ČH3
H
356
85
CH3-OH
381
91
(CH3)3C-H
381
91
(CH3)3C-F
444
106
464
111
(CH3);C-CI
331
79
H3C-ċ-x
(CH)3С — Br
272
65
364
87
(CH3)3C-
209
50
H-F
569
136
CH3CH2-H
410
98
(CH3)3C-OH
381
91
H-CI
431
103
CH;CH2-F
448
107
H-Br
368
88
CH3CH2-CI
339
81
X-X bonds
297
71
CH;CH2-Br
285
68
F-F
159
38
H-OH
498
119
CH3CH2H
222
53
Cl-CI
243
58
H-OCH2CH3
435
104
CH3CH2-OH
381
91
Br-Br
193
46
151
36
C-C bonds
CH3
Но-ОН
213
51
CH3-CH3
H3C-C-x
368
88
CH3CH2-CH3
356
85
H
(CH3)2CH-CH3
351
84
(CH3)2CH-H
397
95
5. In each of the following cases compare the bond identified in red, and determine which
bond you would expect to have largest bond dissociation energy?
CI
F
(a)
(b) Br
Transcribed Image Text:TABLE 6.1 BOND DISSOCIATION ENERGIES (AHº) OF COMMON BONDS KJ/MOL KCAL/MOL KJ/MOL KCAL/MOL KJ/MOL KCAL/MOL Bonds to H H2C=CH-CH3 385 92 (CH3)2CH-F 444 106 H-H 435 104 HC=C-CH3 489 117 (CH3)2CH-C 335 80 H-CH3 435 104 (CH3)½CH-Br 285 68 H-CH2CH3 410 98 Bonds to methyl (CH3)2CH- 222 53 H-CH(CH3)2 397 95 CH3-H 435 104 (CH3)2CH-OH 381 91 H-C(CH3)3 381 91 CH;-F 456 109 473 113 CH3-CI 351 84 CH3 H3C-C-x CH3-Br 293 70 CH3H 234 56 ČH3 H 356 85 CH3-OH 381 91 (CH3)3C-H 381 91 (CH3)3C-F 444 106 464 111 (CH3);C-CI 331 79 H3C-ċ-x (CH)3С — Br 272 65 364 87 (CH3)3C- 209 50 H-F 569 136 CH3CH2-H 410 98 (CH3)3C-OH 381 91 H-CI 431 103 CH;CH2-F 448 107 H-Br 368 88 CH3CH2-CI 339 81 X-X bonds 297 71 CH;CH2-Br 285 68 F-F 159 38 H-OH 498 119 CH3CH2H 222 53 Cl-CI 243 58 H-OCH2CH3 435 104 CH3CH2-OH 381 91 Br-Br 193 46 151 36 C-C bonds CH3 Но-ОН 213 51 CH3-CH3 H3C-C-x 368 88 CH3CH2-CH3 356 85 H (CH3)2CH-CH3 351 84 (CH3)2CH-H 397 95 5. In each of the following cases compare the bond identified in red, and determine which bond you would expect to have largest bond dissociation energy? CI F (a) (b) Br
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