Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 7.SE, Problem 62AP
The heat of hydrogenation for allene (Problem 7-61) to yield propane is -295 kJ/mol, and the heat of hydrogenation for a typical monosubsti- tuted
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Estimate the heat released when ethene(CH2=CH2) reacts with HBr to giveCH3CH2Br. Bond enthalpies areC-H : 412 kJ/mol; C-C : 348 kJ/mol;C=C : 612 kJ/mol; C-Br : 276 kJ/mol;Br-Br : 193 kJ/mol; H-Br : 366 kJ/mol.
Choose the correct answer:1. 1036 kJ/mol2. 58 kJ/mol3. 424 kJ/mol4. 200 kJ/mol5. 470 kJ/mol
7.
The reaction of methoxide anion with
bromoethane to yield the ether ethyl methyl ether and
the bromide anon (Br-) is an excellent example of a
general reaction type called Sy2 (substitution
nucleophilic bimolecular):
CH,0+ CH,СH-Br a CH3-0-CH,СH; + Br-
a. Change in enthalpy is -103 kJ/mol; the change in
entropy is + 0.025 kJ/mol-K. Calculate DG at
300K.
b. Is the reaction endergonic or exergonic?
c. Is the reaction endothermic or exothermic?
d. Use curved arrows to show the complete
mechanism.
Reaction of 2-methyl-1-butene with H-Cl could
yield TWO alkyl chloride products. Draw and name
8.
them.
Using the table of bond energies estimate the heat of combustion of one mole of 2,4-dimethyl-1,3-pentadiene.
Chapter 7 Solutions
Organic Chemistry
Ch. 7.2 - Calculate the degree of unsaturation in each of...Ch. 7.2 - Prob. 2PCh. 7.2 - Diazepam, marketed as an antianxiety medication...Ch. 7.3 - Give IUPAC names for the following compounds:Ch. 7.3 - Prob. 5PCh. 7.3 - Prob. 6PCh. 7.3 - Prob. 7PCh. 7.4 - Prob. 8PCh. 7.4 - Prob. 9PCh. 7.4 - Prob. 10P
Ch. 7.5 - Which member in each of the following sets ranks...Ch. 7.5 - Prob. 12PCh. 7.5 - Prob. 13PCh. 7.5 - Prob. 14PCh. 7.6 - Prob. 15PCh. 7.8 - Prob. 16PCh. 7.8 - Prob. 17PCh. 7.9 - Show the structures of the carbocation...Ch. 7.9 - Draw a skeletal structure of the following...Ch. 7.10 - Prob. 20PCh. 7.11 - On treatment with HBr, vinylcyclohexane undergoes...Ch. 7.SE - Prob. 22VCCh. 7.SE - Prob. 23VCCh. 7.SE - The following carbocation is an intermediate in...Ch. 7.SE - Prob. 25VCCh. 7.SE - Predict the major product and show the complete...Ch. 7.SE - Prob. 27MPCh. 7.SE - When 1, 3-butadiene reacts with one mole of HBr,...Ch. 7.SE - When methyl vinyl ether reacts with a strong acid,...Ch. 7.SE - Addition of HCl to 1-isopropylcyclohexene yields a...Ch. 7.SE - Addition of HCl to...Ch. 7.SE - Limonene, a fragrant hydrocarbon found in lemons...Ch. 7.SE - Prob. 33MPCh. 7.SE - Calculate the degree of unsaturation in the...Ch. 7.SE - Prob. 35APCh. 7.SE - Prob. 36APCh. 7.SE - Name the following alkenes:Ch. 7.SE - Draw structures corresponding to the following...Ch. 7.SE - Prob. 39APCh. 7.SE - Prob. 40APCh. 7.SE - Prob. 41APCh. 7.SE - Prob. 42APCh. 7.SE - Prob. 43APCh. 7.SE - Draw and name the 17 alkene isomers, C6H12,...Ch. 7.SE - Prob. 45APCh. 7.SE - Prob. 46APCh. 7.SE - Which of the following E, Z designations are...Ch. 7.SE - Prob. 48APCh. 7.SE - trans-2-Butene is more stable than cis-2-butene by...Ch. 7.SE - Prob. 50APCh. 7.SE - Normally, a trans alkene is more stable than its...Ch. 7.SE - trans-Cyclooctene is less stable than...Ch. 7.SE - Prob. 53APCh. 7.SE - Prob. 54APCh. 7.SE - Use Hammond’s Postulate to determine which...Ch. 7.SE - Prob. 56APCh. 7.SE - Predict the major product in each of the following...Ch. 7.SE - Prob. 58APCh. 7.SE - Prob. 59APCh. 7.SE - Prob. 60APCh. 7.SE - Allene (1,2-propadiene), H2C=C=CH2, has two...Ch. 7.SE - The heat of hydrogenation for allene (Problem...Ch. 7.SE - Retin A, or retinoic acid, is a medication...Ch. 7.SE - Prob. 64APCh. 7.SE - tert-Butyl esters [RC02C(CH3)3] are converted into...Ch. 7.SE - Vinylcyclopropane reacts with HBr to yield a...Ch. 7.SE - Prob. 67APCh. 7.SE - Prob. 68APCh. 7.SE - Prob. 69APCh. 7.SE - Prob. 70APCh. 7.SE - Prob. 71APCh. 7.SE - Reaction of 2, 3-dimethyl-l-butene with HBr leads...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- From the data in Figure 4-12 and Table 4-1, estimate the percentages of molecules that have their substituents in an axial orientation for the following compounds: (a) Isopropylcyclohexane (b) Fluorocyclohexane (c) Cyclohexanecarbonitrile, C6H11CNarrow_forwardPredict the energy difference between pent-1-ene and cis-pent-2-ene.arrow_forward6. Complete the following reactons: H,SO, HO, ÇH3 H,SO, 4 CH3-C-CH,-CH3 K,Cr,O, H,SO, 4 HO,arrow_forward
- An alkene having the molecular formula C7H₁4 is treated sequentially with ozone (03) and zinc/acetic acid to give the product/s shown. H3CO || CH3CHCH + H3C Draw a structural formula for the alkene. *8 CH3 • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. On [] ? Ⓡ ChemDoodleⓇarrow_forwardIf a catalyst could be found that would establish an equilibrium between 1,2-butadiene and 2-butyne, what would be the ratio of the more stable isomer to the less stable isomer at 25°C? CH,=C=CHCH, CH,C=CCH, AG° = -16.7 kJ (-4.0 kcal)/molarrow_forwardUsing the table of bond energies estimate the heat of combustion of 2-methyl-3-hexyne.arrow_forward
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- Which will be more stable, cis or trans-1,4-tert-butylcyclohexane? Explain by drawing their structures?arrow_forwardbest condition for the reaction (1r,2s)-1 bromo-2methylcyclohexane->(s)3-methylcyclohex-1enearrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step. heat C,H,ONa + CH,=CHCI C,H,OH CI Bicyclo-2,5-heptadienearrow_forward
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