Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 7, Problem 7.53AP
Interpretation Introduction
Interpretation:
The stereoisomer of
Concept introduction:
In presence of peroxide, alkene is oxidized to
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5) Compound A reacted with Mg in ether to give B. Compound B is with Ethyl bromide to give
Ethyl cyclohexane. What are the structures of A and B?
a) When (Z)-3-methylhex-3-ene undergoes hydroboration–oxidation, two isomeric products are formed. Give their structures, and label each asymmetric carbon atom as (R) or (S). What is the relationship between these isomers?
The rate law for addition of Br2Br2 to an alkene is first order in Br2Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2Br2 to an alkene proceeds in the same manner as for addition of HBr? Explain.
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 7.1PCh. 7 - Prob. 7.2PCh. 7 - Prob. 7.3PCh. 7 - Prob. 7.4PCh. 7 - Prob. 7.5PCh. 7 - Prob. 7.6PCh. 7 - Prob. 7.7PCh. 7 - Prob. 7.8PCh. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Prob. 7.13PCh. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Prob. 7.16PCh. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Prob. 7.22PCh. 7 - Prob. 7.23PCh. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - Prob. 7.26PCh. 7 - Prob. 7.27PCh. 7 - Prob. 7.28PCh. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Prob. 7.31PCh. 7 - Prob. 7.32PCh. 7 - Prob. 7.33PCh. 7 - Prob. 7.34APCh. 7 - Prob. 7.35APCh. 7 - Prob. 7.36APCh. 7 - Prob. 7.37APCh. 7 - Prob. 7.38APCh. 7 - Prob. 7.39APCh. 7 - Prob. 7.40APCh. 7 - Prob. 7.41APCh. 7 - Prob. 7.42APCh. 7 - Prob. 7.43APCh. 7 - Prob. 7.44APCh. 7 - Prob. 7.45APCh. 7 - Prob. 7.46APCh. 7 - Prob. 7.47APCh. 7 - Prob. 7.48APCh. 7 - Prob. 7.49APCh. 7 - Prob. 7.50APCh. 7 - Prob. 7.51APCh. 7 - Prob. 7.52APCh. 7 - Prob. 7.53APCh. 7 - Prob. 7.54APCh. 7 - Prob. 7.55APCh. 7 - Prob. 7.56APCh. 7 - Prob. 7.57APCh. 7 - Prob. 7.58APCh. 7 - Prob. 7.59APCh. 7 - Prob. 7.60APCh. 7 - Prob. 7.61APCh. 7 - Prob. 7.62APCh. 7 - Prob. 7.63APCh. 7 - Prob. 7.64APCh. 7 - Prob. 7.65APCh. 7 - Prob. 7.66APCh. 7 - Prob. 7.67APCh. 7 - Prob. 7.68APCh. 7 - Prob. 7.69APCh. 7 - Prob. 7.70APCh. 7 - Prob. 7.71APCh. 7 - Prob. 7.72APCh. 7 - Prob. 7.73APCh. 7 - Prob. 7.74APCh. 7 - Prob. 7.75AP
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- When bromine is added to two beakers, one containing phenyl isopropyl ether and the other containing cyclohexene, the bromine color in both beakers disappears. What observation could you make while performing this test that would allow you to distinguish the alkene from the aryl ether?arrow_forwardBiphenyl has the following structure.(a) Is biphenyl a (fused) polynuclear aromatic hydrocarbon?(b) How many pi electrons are there in the two aromatic rings of biphenyl? How does this number compare with that for naphthalene?(c) The heat of hydrogenation for biphenyl is about 418 kJ>mol (100 kcal>mol). Calculate theresonance energy of biphenyl.(d) Compare the resonance energy of biphenyl with that of naphthalene and with that of two benzene rings. Explain thedifference in the resonance energies of naphthalene and biphenyl.arrow_forwardCompound W has molecular formula C₁4H18 and reacts with H₂ to form X. Oxidative cleavage of W with O3 followed by CH3 SCH3 affords Y. What is the structure of W?arrow_forward
- Alkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)1-Methylcyclohexenearrow_forwardDraw the structure(s) of all of the alkene isomers, C5H10, that contain a branched chain. Consider E/Z stereochemistry of alkenes.arrow_forwardAlkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.) Propenearrow_forward
- Compound A has the formula C8H8. It reacts rapidly with KMN04 to give CO2 and a carboxylic acid, B (C7H602), but reacts with only 1 molar equivalent of H2 on catalytic hydrogenation over a palladium catalyst. On hydrogenation under conditions that reduce aromatic rings, 4, equivalents of H2 are taken up and hydrocarbon C (C8H16) is produced. What are the structures of A, B, and C. .CO.H COH A A B C OH A CO2H A B QUESTION 6arrow_forwardAlkenes can be hydrated to form alcohols by (1) hydroboration followed by oxidation with alkaline hydrogen peroxide and (2) acid-catalyzed hydration. Compare the product formed from each alkene by sequence (1) with those formed from (2). Q.)Cyclopentenearrow_forwardAn organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.arrow_forward
- The rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.arrow_forwardThe rate law for addition of Br2 to an alkenes is first order in Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2 to an alkene proceeds in the same matter as for addition of HBr? Explain.arrow_forwardA hydrocarbon (X), with the molecular formula: C8H14 is reduced in presence of sodium and liquid ammonia to give the only product (Y) with the molecular formula: C8H16. Compounds X and Y both resulting 2,5-dimethylhexane when treated with hydrogen and platinum catalyst (H2/Pt). As a result of the oxidative cleavage of compound Y (by using KMnO4 / H2SO4), a single carboxylic acid derivative with C4H8O2 molecular formula is formed. Again, as a result of the reaction of Y with perbenzoic acid, the chiral compound C8H14O is observed, but the reaction of compound Y with bromine gives the achiral C8H14Br2 as the product.arrow_forward
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