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Bond Enthalpy Bonds to secondary carbons kamol 104 kcalimol (CHCH-H (CHCH-F (CH) CH-CI (CH CH-Br (CH) CH-1 (CH CH-O 105 54 413 40 37 463 57 90 356 45 49 570 309 74 36 238 57 136 432 Bonds to tertiary carbons 95 103 366 (CH,)C-H 88 403 96 298 (CHC-F 71 464 497 (CHC-CI 119 355 85 382 (CH C-Br 304 73 91 367 (CH,)C-I 233 56 88 (CH3)C-OH Other C-H bonds 213 401 96 51 450 108 PHCH,-H (benzylic) 376 372 H,C=CHCH,-H (allylic) НС- СН - Н (vinyl) 439 105 463 481 115 472 Ph-H (aromatic) 350 84 HC=C-H (acetylenic) 558 302 72 C-C bonds 377 241 58 CH,-CH3 372 385 92 CH;CH-CH3 368 356 85 CH;CH2-CH;CH, 371 (CH3),CH–CH3 366 (CH)C-CH;

Bond Enthalpy Bonds to secondary carbons kamol 104 kcalimol (CHCH-H (CHCH-F (CH) CH-CI (CH CH-Br (CH) CH-1 (CH CH-O 105 54 413 40 37 463 57 90 356 45 49 570 309 74 36 238 57 136 432 Bonds to tertiary carbons 95 103 366 (CH,)C-H 88 403 96 298 (CHC-F 71 464 497 (CHC-CI 119 355 85 382 (CH C-Br 304 73 91 367 (CH,)C-I 233 56 88 (CH3)C-OH Other C-H bonds 213 401 96 51 450 108 PHCH,-H (benzylic) 376 372 H,C=CHCH,-H (allylic) НС- СН - Н (vinyl) 439 105 463 481 115 472 Ph-H (aromatic) 350 84 HC=C-H (acetylenic) 558 302 72 C-C bonds 377 241 58 CH,-CH3 372 385 92 CH;CH-CH3 368 356 85 CH;CH2-CH;CH, 371 (CH3),CH–CH3 366 (CH)C-CH;

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry
Section4.7: Conformations Of Monosubstituted Cyclohexanes
Problem 17P: Look at Figure 4-12 on page 105, and estimate the percentages of axial and equatorial conformations...
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Question 4-41 a) and b)
Bond-Dissociation Enthalpies for Homolytic Cleavages Enthaley TABLE 4-2 4-7 Enthalpy Changes in Chlorination 167 Bond-Dissociation AB A Enthalpy k/mol Bond kcalimol X bonds and X-Xbonds Bond-Dissociation Bond 436 Enthalpy 104 Bonds to secondary cartons 440 kalmol kealimol D-D (CH) CH-H (CH) CH-F (CH) CH-CI (CH) CH-Br 105 154 F-F gent) 37 240 413 99 CI-CI 57 463 190 Br Br olyti 356 45 149 1-1 (CH),CH-1 epend 309 74 36 570 (CH) CH-OH 238 H-F 57 136 432 399 much Bonds to tertiary carbons H-CI 95 103 366 (CH))C-H w the used H-Br 88 298 403 96 (CH)C-F H-I 71 464 497 (CH)C-CI Но-н 119 355 85 cd to endo. 382 (CH)C-Br HS-H 91 304 73 367 (CH)C-1 HOO-H 88 233 56 ation (CH3),C-OH 213 401 96 51 of the HO-OH Other C-H bonds 450 108 H,N-H PHCH,-H (benzylic) HC=CHCH2-H (allylic) H,C=CH-H (vinyl) 376 90 Methyl bonds -H 439 372 89 105 CH3- 11 463 481 115 CH;-F Ph-H (aromatic) 472 113 350 84 HC=C-H(acetylenic) 558 133 CH-CI 302 72 C-C bonds CH-Br D) 241 58 CH3-CH3 377 90 CH-1 89 385 92 CH;CH2-CH3 372 have ond- CH — ОН 88 356 85 CH;CH2-CH;CH3 368 371 89 CH;-NH2 (CH3),CH-CH3 87 366 Bonds to primary carbons 101 423 (CH3),C-CH3 111* C=C and C=X bonds CH;CH-H 464* 728 174 85 H2C=CH2 CH,CH-F 355 176 736 72 H,C=NH CH,CH2 CI 179 303 749 tion H2C=0 57 CH;CH2-Br 238 ond nd a 94 CH,CH-I 393 101 CH,CH-OH 423 111* CH3CH,CH-H 464* 85 CH;CH,CH-F 355 72 CH;CH,CH-CI 303 57 CH;CH;CH,-Br 238 CH,CH,CH-I approximate
Transcribed Image Text:Bond-Dissociation Enthalpies for Homolytic Cleavages Enthaley TABLE 4-2 4-7 Enthalpy Changes in Chlorination 167 Bond-Dissociation AB A Enthalpy k/mol Bond kcalimol X bonds and X-Xbonds Bond-Dissociation Bond 436 Enthalpy 104 Bonds to secondary cartons 440 kalmol kealimol D-D (CH) CH-H (CH) CH-F (CH) CH-CI (CH) CH-Br 105 154 F-F gent) 37 240 413 99 CI-CI 57 463 190 Br Br olyti 356 45 149 1-1 (CH),CH-1 epend 309 74 36 570 (CH) CH-OH 238 H-F 57 136 432 399 much Bonds to tertiary carbons H-CI 95 103 366 (CH))C-H w the used H-Br 88 298 403 96 (CH)C-F H-I 71 464 497 (CH)C-CI Но-н 119 355 85 cd to endo. 382 (CH)C-Br HS-H 91 304 73 367 (CH)C-1 HOO-H 88 233 56 ation (CH3),C-OH 213 401 96 51 of the HO-OH Other C-H bonds 450 108 H,N-H PHCH,-H (benzylic) HC=CHCH2-H (allylic) H,C=CH-H (vinyl) 376 90 Methyl bonds -H 439 372 89 105 CH3- 11 463 481 115 CH;-F Ph-H (aromatic) 472 113 350 84 HC=C-H(acetylenic) 558 133 CH-CI 302 72 C-C bonds CH-Br D) 241 58 CH3-CH3 377 90 CH-1 89 385 92 CH;CH2-CH3 372 have ond- CH — ОН 88 356 85 CH;CH2-CH;CH3 368 371 89 CH;-NH2 (CH3),CH-CH3 87 366 Bonds to primary carbons 101 423 (CH3),C-CH3 111* C=C and C=X bonds CH;CH-H 464* 728 174 85 H2C=CH2 CH,CH-F 355 176 736 72 H,C=NH CH,CH2 CI 179 303 749 tion H2C=0 57 CH;CH2-Br 238 ond nd a 94 CH,CH-I 393 101 CH,CH-OH 423 111* CH3CH,CH-H 464* 85 CH;CH,CH-F 355 72 CH;CH,CH-CI 303 57 CH;CH;CH,-Br 238 CH,CH,CH-I approximate
In the presence of a small amount of bromine, the following light-promoted reaction has been observed. Label each hydrogen atom in the following compounds as primary (1°), secondary (2), or tertiary (3 (b) (CH), ССH,CH, 198 The Study of Chemical Reactions CHAPTER 4 (c) (CH,),CHCH(CH,)CHSH 4-40 H CH, (a) CH,CH,CH(CH)2 4- CH3 (f) CH (e) (d) Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of AH° for the following reactione (a) CH3-CH3 + I (b) CH;CH, CI + HI (c) (CH;);C-OH + HCI (d) CH;CH, CH; + H2 (e) CH; CH,OH + Use the information in Table 4-2 (p. 167) to rank the following radicals in decreasing order of stability. 4-41 CH; CH,I + HI CH; CH,I + HCI (CH3);C-CI + H,O CH CH; + CH CH, CH,-Br + H,0 HBr 4-42 (CH,),CH 1-CH, •CH, CH,CH, CH, (CH,),C. CH,=CH- 4-43 For each alkane, 1. draw all the possible monochlorinated derivatives. 2. determine whether free-radical chlorination would be a good way to make.any of these monochlorinated deriva (Will the reaction give mostly one major product?) 3. which monobrominated derivatives could you form in good yield by free-radical bromination? (a) cyclopentane (c) 2-methylpentane Write a mechanism for the light-initiated reaction of cyclohexane with chlorine to give chlorocyclohexane. Label te initiation and propagation steps. (b) methylcyclopentane (d) 2,2,3,3-tetramethylbutane 4-44 Cl hv Cl, HCL cyclohexane chlorocyclohexane 445 Draw the important resonance forms of the following free radicals in, (a) CH, CH-CH, (b) -CH, (c) CH, -C-O· (d) (e) (f) 4-46 H.C CH H3C CH3 hv Br2 H2C Br CH3
Transcribed Image Text:In the presence of a small amount of bromine, the following light-promoted reaction has been observed. Label each hydrogen atom in the following compounds as primary (1°), secondary (2), or tertiary (3 (b) (CH), ССH,CH, 198 The Study of Chemical Reactions CHAPTER 4 (c) (CH,),CHCH(CH,)CHSH 4-40 H CH, (a) CH,CH,CH(CH)2 4- CH3 (f) CH (e) (d) Use bond-dissociation enthalpies (Table 4-2, p. 167) to calculate values of AH° for the following reactione (a) CH3-CH3 + I (b) CH;CH, CI + HI (c) (CH;);C-OH + HCI (d) CH;CH, CH; + H2 (e) CH; CH,OH + Use the information in Table 4-2 (p. 167) to rank the following radicals in decreasing order of stability. 4-41 CH; CH,I + HI CH; CH,I + HCI (CH3);C-CI + H,O CH CH; + CH CH, CH,-Br + H,0 HBr 4-42 (CH,),CH 1-CH, •CH, CH,CH, CH, (CH,),C. CH,=CH- 4-43 For each alkane, 1. draw all the possible monochlorinated derivatives. 2. determine whether free-radical chlorination would be a good way to make.any of these monochlorinated deriva (Will the reaction give mostly one major product?) 3. which monobrominated derivatives could you form in good yield by free-radical bromination? (a) cyclopentane (c) 2-methylpentane Write a mechanism for the light-initiated reaction of cyclohexane with chlorine to give chlorocyclohexane. Label te initiation and propagation steps. (b) methylcyclopentane (d) 2,2,3,3-tetramethylbutane 4-44 Cl hv Cl, HCL cyclohexane chlorocyclohexane 445 Draw the important resonance forms of the following free radicals in, (a) CH, CH-CH, (b) -CH, (c) CH, -C-O· (d) (e) (f) 4-46 H.C CH H3C CH3 hv Br2 H2C Br CH3
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