Question 1a. (0.5 point) Consider the bond dissociation energies listed below in kcal/mol CH3 – Br...
Question 1a. (0.5 point) Consider the bond dissociation energies listed below in kcal/mol
CH3 – Br 70
CH3CH2 – Br 68
(CH3)2CH – Br 68
(CH3)3C – Br 65
These data show that the carbon–bromine bond is weakest when bromine is bound to a ____.
a) methyl carbon
b) primary carbon
c) secondary carbon
d) tertiary carbon
e) quaternary carbon
1b. Predict the product for the halogenation reaction given below when methyl cyclohexane is subjected to free radical bromination Br2 hv (1 point)
Now, write the complete mechanism for this product (3 points)
Homework Answers
When bromine is attached to tertiary carbon the bond between br-C is the weakest as you can see in the table.... With less bond dissociation energy
It can easily break and we will get a stable tertiary carbocation.
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Question 1a. (0.5 point) Consider the bond dissociation energies
listed below in kcal/mol
CH3 – Br...
7. Calculate the AHRxn for the following transformation. A table of bond dissociation energies is provided...
7. Calculate the AHRxn for the following transformation. A table of bond dissociation energies is provided below. All work must be shown for partial credit. (8 pts.) hv Br + Br-Br + HBr: Table of Selected Homolytic Bond Dissociation Energies. Bond Broken (CH3)3C-H (CH3)2CH-H Br-Br H-Br CH3CH2-H (CH3)3C-Br (CH3)2CH-Br CH3CH2-Br kJ/mol 400 413 193 366 421 292 298 295
TABLE 6.1 BOND DISSOCIATION ENERGIES (A) OF COMMON BONDS KJ/MOL KCAL/MOL Bonds to H H2C=CH-CH2 HCC-CH,...
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1. Bond Dissociation Energies and Free Radicals Bond Bond Dissociation Energies (kJ/mol) Bond BDE Bond BDE (kJ/mol) (kJ/mol) H-H 436 CH3-H 439 H-F 570 CH3CH2-H 432 H-CI 432 (CH3CH2 413 BDE Bond (kJ/mol) 10-N 350 0-0 180 F-F O-H 0-C O-F 460 BDE (kJ/mol) | 200 180 159 | H-Br H-I 366 298 404 350 O-C1200 O-Br (CH3)3C-H C-C (sigma) C=C(pi) 210 C1-C1243 Br-Br 193 243 0 -I 220 I-I | 151 A. The enzyme methane monooxygenase catalyzes a remarkably...
Based on the information gathered in (1a), predict the product for the halogenation reaction given below...
Based on the information gathered in (1a), predict the product for the halogenation reaction given below when methyl cyclohexane is subjected to free radical bromination (1 point) Br2 hv Now, write the complete mechanism for this product (3 points) Q2. Draw the product for (1 point) au -
Problem #3 Calculate AH° for the following reaction using the bond energies found in Table 6.1...
Problem #3 Calculate AH° for the following reaction using the bond energies found in Table 6.1 on page 228. Is this reaction spontaneous? (CH3)3C-H + 12 (CH3)3C-1 + HI TABLE 6.1 BOND DISSOCIATION ENERGIES (AH) OF COMMON BONDS KJ/MOL KCAL/MOL H2C=CH-CH3 HC-C-CH KJ/MOL KCAL/MOL 385 92 489117 KJ/MOL KCAL/MOL 444 106 335 80 285 Bonds to H. H-H H-CH3 H-CH2CH3 H-CH(CH3)2 H-C(CH3)3 (CH3)2CH-F (CH3)2CH-CI (CH3)2CH-Br (CH3)2CH- (CH3)2CH-OH 68 222 435 104 435 104 41098 39795 91 473 113 53 381...
Bond Dissociation Energies, Dº298, for X-Y kJ/mol (kcal/mol) X\Y= H F Ci Br I OH NH2...
Bond Dissociation Energies, Dº298, for X-Y kJ/mol (kcal/mol) X\Y= H F Ci Br I OH NH2 CH3 CH3CH2- CN CH3- CH3CH2 (CH3)2CH- 439 (105) 452 (108) 356 (85) 293 (70) 423 (101) 444 (106) 335 (80) 285 (68) 238 (57) 385 (92) 356 (85) 377 (90) 368 (88) 510 (122) 228 (53) 380 (91) 356 (85) 368 (88) 336 (80) 409 (98) 448 (107) 339 (81) 274 (65) 226 (54) 385 (92) 351(84) 331 (79) 263 (63) 213 (51) 380...
What is Wrong? Select the keyword or phrase that will best complete each sentence. Key terms: A radical...
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Select the keyword or phrase that will best complete each sentence. Key terms: A radical is a reactive intermediate with a single unpaired electron, formed by homoloysis of a covalent bond. paired unpaired Allylic radicals are stabilized by resonance, making them more stable than tertiary radicals increases inductive effects A compound that contains an especially weak bond that serves as a source of radicals is called a radical initiator ess homoloysis decreases more J Treatment of cyclohexene...
Mechanisms Question 1 (22 marks) (a) Consider the radical chain reactions of the alkane shown below with Br, in the...
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7. Calculate the AHRxn for the following transformation. A table of bond dissociation energies is provided below. All work must be shown for partial credit. (8 pts.) hv Br + Br-Br + HBr: Table of Selected Homolytic Bond Dissociation Energies. Bond Broken (CH3)3C-H (CH3)2CH-H Br-Br H-Br CH3CH2-H (CH3)3C-Br (CH3)2CH-Br CH3CH2-Br kJ/mol 400 413 193 366 421 292 298 295
TABLE 6.1 BOND DISSOCIATION ENERGIES (A) OF COMMON BONDS KJ/MOL KCAL/MOL Bonds to H H2C=CH-CH2 HCC-CH, KJ/MOL KCAL/MOL 385 92 489117 HH 435 80 104 104 KJ/MOL KCAL/MOL 444 106 335 285 222 381 91 (CH3)2CH-F (CH) CH-CI (CH3)2CHBr (CH),CH (CH3)2CH-OH H-CH3 H-CH2CH3 HCH(CH3 H- CH3) 435 104 109 Bonds to methyl CH; CHEF CH3-C1 CH3-Br CH3 CH, OH CH I I 356 85 381 91 HC-c-X CHE (CH3)3C-H (CH3),C-F (CH),C-C1 (CH3)2C-Br (CH3), (CH)C-OH 381 444 331 106 111 464...
Bond Dissociation Energies (for A-B Bond broken AH, kJ/mol Bond broken → A A4, kJ/mol + B) Bond broken mo H-H CH3CH2CH2-H (CH3)2CH-H (CH3)3C-H 436 423 413 400. H-Br 366 CH3CH2CH2-Br 294 (CH3)2CH-Br 298 (CH3)3C-Br292 Br-Br 193 H-CI 432 CH3CH2CH2-CI 354 (CH3)2CH-CI 355 (CH3)3C-CI 349 CI-CI 243 Alkane halogenation is a two-step reaction, as shown below. Using the table of bond dissociation energies, calculate the enthalpy of each step and the enthalpy of the overall reaction. Step 1: Number CH3CHCH3...
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1. Bond Dissociation Energies and Free Radicals Bond Bond Dissociation Energies (kJ/mol) Bond BDE Bond BDE (kJ/mol) (kJ/mol) H-H 436 CH3-H 439 H-F 570 CH3CH2-H 432 H-CI 432 (CH3CH2 413 BDE Bond (kJ/mol) 10-N 350 0-0 180 F-F O-H 0-C O-F 460 BDE (kJ/mol) | 200 180 159 | H-Br H-I 366 298 404 350 O-C1200 O-Br (CH3)3C-H C-C (sigma) C=C(pi) 210 C1-C1243 Br-Br 193 243 0 -I 220 I-I | 151 A. The enzyme methane monooxygenase catalyzes a remarkably...
Based on the information gathered in (1a), predict the product for the halogenation reaction given below when methyl cyclohexane is subjected to free radical bromination (1 point) Br2 hv Now, write the complete mechanism for this product (3 points) Q2. Draw the product for (1 point) au -
Problem #3 Calculate AH° for the following reaction using the bond energies found in Table 6.1 on page 228. Is this reaction spontaneous? (CH3)3C-H + 12 (CH3)3C-1 + HI TABLE 6.1 BOND DISSOCIATION ENERGIES (AH) OF COMMON BONDS KJ/MOL KCAL/MOL H2C=CH-CH3 HC-C-CH KJ/MOL KCAL/MOL 385 92 489117 KJ/MOL KCAL/MOL 444 106 335 80 285 Bonds to H. H-H H-CH3 H-CH2CH3 H-CH(CH3)2 H-C(CH3)3 (CH3)2CH-F (CH3)2CH-CI (CH3)2CH-Br (CH3)2CH- (CH3)2CH-OH 68 222 435 104 435 104 41098 39795 91 473 113 53 381...
Bond Dissociation Energies, Dº298, for X-Y kJ/mol (kcal/mol) X\Y= H F Ci Br I OH NH2 CH3 CH3CH2- CN CH3- CH3CH2 (CH3)2CH- 439 (105) 452 (108) 356 (85) 293 (70) 423 (101) 444 (106) 335 (80) 285 (68) 238 (57) 385 (92) 356 (85) 377 (90) 368 (88) 510 (122) 228 (53) 380 (91) 356 (85) 368 (88) 336 (80) 409 (98) 448 (107) 339 (81) 274 (65) 226 (54) 385 (92) 351(84) 331 (79) 263 (63) 213 (51) 380...
What is Wrong?
Select the keyword or phrase that will best complete each sentence. Key terms: A radical is a reactive intermediate with a single unpaired electron, formed by homoloysis of a covalent bond. paired unpaired Allylic radicals are stabilized by resonance, making them more stable than tertiary radicals increases inductive effects A compound that contains an especially weak bond that serves as a source of radicals is called a radical initiator ess homoloysis decreases more J Treatment of cyclohexene...
Mechanisms Question 1 (22 marks) (a) Consider the radical chain reactions of the alkane shown below with Br, in the presence of light. H3C HH H C-CCHS CH3 Br2 hv 2 Different mono- bromo products 25 °C + (you will need to look up the bond dissociation energy (BDE) for the types of bonds formed and broken in this reactions) (i) Give the structures of the products from the reaction and using standard arrow conventions show the series of mechanistic...
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