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Which of the conjugate bases of the following compounds will be strong enough to deprotonate CH3CH2OH? Indicate all that apply. a. С4Н10 Ob. NH3 Oc. C2H2 Od. CH3CH2CO2H O e. H Of. HBr

Which of the conjugate bases of the following compounds will be strong enough to deprotonate CH3CH2OH? Indicate all that apply. a. С4Н10 Ob. NH3 Oc. C2H2 Od. CH3CH2CO2H O e. H Of. HBr

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter20: Carboxylic Acids And Nitriles
Section20.3: Biological Acids And The Henderson–hasselbalch Equation
Problem 5P: Calculate the percentages of dissociated and undissociated forms present in the following solutions:...
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Which of the conjugate bases of the following compounds will be strong enough to deprotonate CH3CH2OH? Indicate all that apply. a. С4Н10 O b. NH3 Oc. C2H2 Od. CH3CH2CO2H O e. H |f. HBr
Transcribed Image Text:Which of the conjugate bases of the following compounds will be strong enough to deprotonate CH3CH2OH? Indicate all that apply. a. С4Н10 O b. NH3 Oc. C2H2 Od. CH3CH2CO2H O e. H |f. HBr
Average Bond Enthalpies Average Bond Enthalpies Bond C=C CEC C=N KJ/mol 614 839 Bond KJ/mol Bond KJ/mol Bond KJ/mol Bond KJ/mol С-Н 413 N-H 391 O-H 463 F-F 155 146 190 C-C 348 N-N 163 201 0-0 O-F CI-F 253 242 615 891 799 1072 C-N 293 N-O CI-CI CEN C-O C-F C-CI C-Br 358 N-F N-CI 272 O-CI 203 Br-F Br-CI Br-Br 237 485 200 234 218 C=0 328 N-Br 243 193 CEO 276 240 259 S-H S-F S-CI S-Br 339 327 253 218 C-I C-S H-H H-F H-CI H-Br 436 567 431 I-CI I-Br 208 175 151 N=N 418 NEN 941 Si-H 323 Si-Si 226 366 S-S 266 N=O 607 299 Si-C 301 B-H 389 P-H 322 S=0 S=S 523 418 Si-O 368 B-O B-F 536 Si-CI 464 613 B-CI 456 B-Br 377 O2 495 Acid pK, so Solids Naci 72.1 HC=C-H 25 Liquids HBr сH,он 237.6 CH, 228.9 H,0 Ca,(PO 236 Gases HCI | N.O Mg CaCo, 198.7 32.7 MgH, 31.1 29.1 51.4 64.7 27.2 92.9 186.9 219.9 211.2 240.1 304.3 232.0 Cacl, H,C=CH-H 44 N,0 NO 113.8 Li Cа(он), 76.1 Na K Fe 172.8 69.9 216.3 NO, H;C-CH2-H 50 PCI, Cac, glucose 352.7 70.0 209.2 5.6 186.9 B,H, CH NH2-H FeCl, 142.3 35 Gases H, N, 186.3 в B 5.90 130.7 C,H, C,H. C,H, 200.8 219.6 229.6 126.0 146.2 Si I 18.8 NH,CI Ca,(PO, 238.5 Mg(OH), 63.2 191.5 H-H 36 205.1 192.5 238.9 197.7 H,PO, "110 Na,so, 149.6 Na,co, 136.0 NaOH 52.3 Na, PO, 224.7 LICI Mgo MgCl, Naci(aq) 115.5 Не CH,CH,OH 15.9 kJ/mol 2.1 4.2 Ne CI OH Ar 154.8 co, F2 ci, 213.7 202.8 223 310 Kr R-CO2-H 5 164.0 169.6 CH, 55.2 26.8 89.5 7.6 8.0 9.2 22.8 Xe CH,CH, HCI -8 ipr t-Bu Strong Base Weak Base Weak Base Strong Base Weak Nucleophile Strong Nucleophile Strong Nucleophile Weak Nucleophile H', DBN, DBU OH", RO I, Br", CI', RS" HS', RSH, H,S H20, ROH DBN DBU Radical Stability Bond Dissociation Energy, kJ/mole CH, CH;CH; (CH3)2CH2 (CH3);CH allyl-H Benzyl-H phenyl-H vinyl-H 431 410 396 381 356 356 431 427 allyl, benzyl > 3° > 2° > 1° > CH3 Reactions: Can only use Radical, Alkene, Substitution and Elimination.
Transcribed Image Text:Average Bond Enthalpies Average Bond Enthalpies Bond C=C CEC C=N KJ/mol 614 839 Bond KJ/mol Bond KJ/mol Bond KJ/mol Bond KJ/mol С-Н 413 N-H 391 O-H 463 F-F 155 146 190 C-C 348 N-N 163 201 0-0 O-F CI-F 253 242 615 891 799 1072 C-N 293 N-O CI-CI CEN C-O C-F C-CI C-Br 358 N-F N-CI 272 O-CI 203 Br-F Br-CI Br-Br 237 485 200 234 218 C=0 328 N-Br 243 193 CEO 276 240 259 S-H S-F S-CI S-Br 339 327 253 218 C-I C-S H-H H-F H-CI H-Br 436 567 431 I-CI I-Br 208 175 151 N=N 418 NEN 941 Si-H 323 Si-Si 226 366 S-S 266 N=O 607 299 Si-C 301 B-H 389 P-H 322 S=0 S=S 523 418 Si-O 368 B-O B-F 536 Si-CI 464 613 B-CI 456 B-Br 377 O2 495 Acid pK, so Solids Naci 72.1 HC=C-H 25 Liquids HBr сH,он 237.6 CH, 228.9 H,0 Ca,(PO 236 Gases HCI | N.O Mg CaCo, 198.7 32.7 MgH, 31.1 29.1 51.4 64.7 27.2 92.9 186.9 219.9 211.2 240.1 304.3 232.0 Cacl, H,C=CH-H 44 N,0 NO 113.8 Li Cа(он), 76.1 Na K Fe 172.8 69.9 216.3 NO, H;C-CH2-H 50 PCI, Cac, glucose 352.7 70.0 209.2 5.6 186.9 B,H, CH NH2-H FeCl, 142.3 35 Gases H, N, 186.3 в B 5.90 130.7 C,H, C,H. C,H, 200.8 219.6 229.6 126.0 146.2 Si I 18.8 NH,CI Ca,(PO, 238.5 Mg(OH), 63.2 191.5 H-H 36 205.1 192.5 238.9 197.7 H,PO, "110 Na,so, 149.6 Na,co, 136.0 NaOH 52.3 Na, PO, 224.7 LICI Mgo MgCl, Naci(aq) 115.5 Не CH,CH,OH 15.9 kJ/mol 2.1 4.2 Ne CI OH Ar 154.8 co, F2 ci, 213.7 202.8 223 310 Kr R-CO2-H 5 164.0 169.6 CH, 55.2 26.8 89.5 7.6 8.0 9.2 22.8 Xe CH,CH, HCI -8 ipr t-Bu Strong Base Weak Base Weak Base Strong Base Weak Nucleophile Strong Nucleophile Strong Nucleophile Weak Nucleophile H', DBN, DBU OH", RO I, Br", CI', RS" HS', RSH, H,S H20, ROH DBN DBU Radical Stability Bond Dissociation Energy, kJ/mole CH, CH;CH; (CH3)2CH2 (CH3);CH allyl-H Benzyl-H phenyl-H vinyl-H 431 410 396 381 356 356 431 427 allyl, benzyl > 3° > 2° > 1° > CH3 Reactions: Can only use Radical, Alkene, Substitution and Elimination.
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