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formula but different arrangements of atoms. Use Table 8.3 to estimate AH for each of the following gas-phase isomer- ization reactions and indicate which isomer has the lower enthalpy H H I I (а) Н—С—С—0-н — Н-С-0-С-Н Нн Ethanol Dimethyl ether но — Н—С—С—Н (b) Н——С-H T I нн н Acetaldehyde Ethylene oxide Н, Н. н H HHH H I| С—С—С—С-С—Н (c) H Н H н' Pentadiene Cyclopentene Н Н Н-С—NEC — Н—С-СEN (d) Н Н Methyl isocyanide Acetonitrile | Strengths and Lengths 8.8 of Covalent Bonds The stability of a molecule is related to the strengths of its covalent bonds. We saw in Chapter 5 that we can measure the average bond enthalpy of many single bonds (Table 5.4). Table 5.4 is repeated here as Table 8.3. As you might expect, Table 8.3 shows that multiple bonds are generally stronger than single bonds TABLE 8.3 Average Bond Enthalpies (k)J/mol) Single Bonds 413 N-H 391 о--н F-F 463 155 С-н N-N 163 348 О-О 146 С-с N-O 201 293 О-F 190 Cl-F 253 C-N N-F О— СI 272 358 203 Cl-Cl 242 С-о N-CI 200 О-1 485 234 С-F N-Br 243 328 Br-F 237 C-CI 276 S-H 339 Br-Cl 218 С-Br Н--Н 436 SF 240 327 Br-Br 193 С-1 Н-F 567 S-Cl 259 253 С-S Н-СI 431 S-Br 218 I-CI 208 Н- Br 366 323 S-S 266 I--Br Si-H 175 Н-I 299 226 Si-Si I-I 151 301 Si-C 368 Si-O 464 Si-Cl Multiple Bonds C=C 614 N=N 418 O=O 495 C=C 839 N=N 941 C=N 615 N- O 607 S=O 523 C=N 891 S=S 418 C=O 799 C O 1072

formula but different arrangements of atoms. Use Table 8.3 to estimate AH for each of the following gas-phase isomer- ization reactions and indicate which isomer has the lower enthalpy H H I I (а) Н—С—С—0-н — Н-С-0-С-Н Нн Ethanol Dimethyl ether но — Н—С—С—Н (b) Н——С-H T I нн н Acetaldehyde Ethylene oxide Н, Н. н H HHH H I| С—С—С—С-С—Н (c) H Н H н' Pentadiene Cyclopentene Н Н Н-С—NEC — Н—С-СEN (d) Н Н Methyl isocyanide Acetonitrile | Strengths and Lengths 8.8 of Covalent Bonds The stability of a molecule is related to the strengths of its covalent bonds. We saw in Chapter 5 that we can measure the average bond enthalpy of many single bonds (Table 5.4). Table 5.4 is repeated here as Table 8.3. As you might expect, Table 8.3 shows that multiple bonds are generally stronger than single bonds TABLE 8.3 Average Bond Enthalpies (k)J/mol) Single Bonds 413 N-H 391 о--н F-F 463 155 С-н N-N 163 348 О-О 146 С-с N-O 201 293 О-F 190 Cl-F 253 C-N N-F О— СI 272 358 203 Cl-Cl 242 С-о N-CI 200 О-1 485 234 С-F N-Br 243 328 Br-F 237 C-CI 276 S-H 339 Br-Cl 218 С-Br Н--Н 436 SF 240 327 Br-Br 193 С-1 Н-F 567 S-Cl 259 253 С-S Н-СI 431 S-Br 218 I-CI 208 Н- Br 366 323 S-S 266 I--Br Si-H 175 Н-I 299 226 Si-Si I-I 151 301 Si-C 368 Si-O 464 Si-Cl Multiple Bonds C=C 614 N=N 418 O=O 495 C=C 839 N=N 941 C=N 615 N- O 607 S=O 523 C=N 891 S=S 418 C=O 799 C O 1072

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 19E
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formula but different arrangements of atoms. Use Table 8.3 to estimate AH for each of the following gas-phase isomer- ization reactions and indicate which isomer has the lower enthalpy H H I I (а) Н—С—С—0-н — Н-С-0-С-Н Нн Ethanol Dimethyl ether но — Н—С—С—Н (b) Н——С-H T I нн н Acetaldehyde Ethylene oxide Н, Н. н H HHH H I| С—С—С—С-С—Н (c) H Н H н' Pentadiene Cyclopentene Н Н Н-С—NEC — Н—С-СEN (d) Н Н Methyl isocyanide Acetonitrile
Transcribed Image Text:formula but different arrangements of atoms. Use Table 8.3 to estimate AH for each of the following gas-phase isomer- ization reactions and indicate which isomer has the lower enthalpy H H I I (а) Н—С—С—0-н — Н-С-0-С-Н Нн Ethanol Dimethyl ether но — Н—С—С—Н (b) Н——С-H T I нн н Acetaldehyde Ethylene oxide Н, Н. н H HHH H I| С—С—С—С-С—Н (c) H Н H н' Pentadiene Cyclopentene Н Н Н-С—NEC — Н—С-СEN (d) Н Н Methyl isocyanide Acetonitrile
| Strengths and Lengths 8.8 of Covalent Bonds The stability of a molecule is related to the strengths of its covalent bonds. We saw in Chapter 5 that we can measure the average bond enthalpy of many single bonds (Table 5.4). Table 5.4 is repeated here as Table 8.3. As you might expect, Table 8.3 shows that multiple bonds are generally stronger than single bonds TABLE 8.3 Average Bond Enthalpies (k)J/mol) Single Bonds 413 N-H 391 о--н F-F 463 155 С-н N-N 163 348 О-О 146 С-с N-O 201 293 О-F 190 Cl-F 253 C-N N-F О— СI 272 358 203 Cl-Cl 242 С-о N-CI 200 О-1 485 234 С-F N-Br 243 328 Br-F 237 C-CI 276 S-H 339 Br-Cl 218 С-Br Н--Н 436 SF 240 327 Br-Br 193 С-1 Н-F 567 S-Cl 259 253 С-S Н-СI 431 S-Br 218 I-CI 208 Н- Br 366 323 S-S 266 I--Br Si-H 175 Н-I 299 226 Si-Si I-I 151 301 Si-C 368 Si-O 464 Si-Cl Multiple Bonds C=C 614 N=N 418 O=O 495 C=C 839 N=N 941 C=N 615 N- O 607 S=O 523 C=N 891 S=S 418 C=O 799 C O 1072
Transcribed Image Text:| Strengths and Lengths 8.8 of Covalent Bonds The stability of a molecule is related to the strengths of its covalent bonds. We saw in Chapter 5 that we can measure the average bond enthalpy of many single bonds (Table 5.4). Table 5.4 is repeated here as Table 8.3. As you might expect, Table 8.3 shows that multiple bonds are generally stronger than single bonds TABLE 8.3 Average Bond Enthalpies (k)J/mol) Single Bonds 413 N-H 391 о--н F-F 463 155 С-н N-N 163 348 О-О 146 С-с N-O 201 293 О-F 190 Cl-F 253 C-N N-F О— СI 272 358 203 Cl-Cl 242 С-о N-CI 200 О-1 485 234 С-F N-Br 243 328 Br-F 237 C-CI 276 S-H 339 Br-Cl 218 С-Br Н--Н 436 SF 240 327 Br-Br 193 С-1 Н-F 567 S-Cl 259 253 С-S Н-СI 431 S-Br 218 I-CI 208 Н- Br 366 323 S-S 266 I--Br Si-H 175 Н-I 299 226 Si-Si I-I 151 301 Si-C 368 Si-O 464 Si-Cl Multiple Bonds C=C 614 N=N 418 O=O 495 C=C 839 N=N 941 C=N 615 N- O 607 S=O 523 C=N 891 S=S 418 C=O 799 C O 1072
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