Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 7.SE, Problem 25VC
Interpretation Introduction
Interpretation:
The alkyl bromide shown is 1-bromo-1-ethyl-3-methylcyclohexane. The structures of three different
Concept introduction:
In electrophilic addition reactions, the first step is the attack of the π electrons of the double bond on the hydrogen of the hydrogen halide to yield a carbocation. One of the carbon in C = C gets attached to hydrogen while the other acquires a positive charge. In the second step, the carbocation produced reacts with a halide ion to give the
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1. Reaction of 2,3-dimethyl-1-butene with HBr leads to an alkyl bromide, C6H13Br. On treatment of this alkyl halide with KOH in methanol, elimination of HBr occurs and a hydrocarbon that is isometric with the starting alkene is formed. What is the structure of this hydrocarbon and how do you think it is formed from an alkyl bromide?
2. 1-Octen-3-ol is a potent mosquito attractant commonly used in mosquito traps. A number of reactions, including hydrogenation, will transform 1-Octen-3-ol into a less effective molecule.
Write a complete reaction equation for the hydrogenation of this alkenol.
5A
In the following reactions, mixtures of alkenes and ethyl ethers
are formed. Draw their structures. Explain which is or are likely
to be the main product(s) in each reaction. In case of formation
of two isomers of alkenes, explain which is formed in greater
proportion
CH3
ofi
H3C-
-Br
CH3
EtOH
Addition of HBr to 3,3-dimethyl-1-butene gives a mixture of two isomeric alkyl bromide products. Draw structures for the two products, and give a mechanistic explanation for their formation.
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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- Questão 10A certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis resulted in CH3(CH2)4CO2H and HO2CCH2CH2CO2H as the only products. What is the reasonable structure for this hydrocarbon? Hexadec-6,10-dino undec-1,5-dino Hept-1,5-dino hex-1,5-dino naharrow_forwardGive the product and mechanism for the following reaction. Be sure to include all mechanism arrows, lone pairs, and formal charges in your mechanism. The product is an alkene.arrow_forwardIdentify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.arrow_forward
- CCH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Hjö: -CH3 -CH3 H3O*arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_forwardThe structure below is the cyclic ether (epoxide), butene oxide: (1) CH3CH₂ -CH₂ butene oxide How could this compound be prepared from but-1-ene? Explain why butene oxide is much more reactive than its isomer, tetrahydrofuran, which is also a cyclic ether: H₂C-CH₂ H₂C CH₂ tetrahydrofuran Illustrate how butene oxide reacts with ammonia, showing details of the mechanism leading to the final product, C4H11 NO.arrow_forward
- When the given reactions below are done once, which of the following reactions is used to prepare dihalogenated alkyl halides as major products? Select one: O Reaction of ethane with Cl₂ in the presence of light Reaction of ethene with HBr Reaction of ethyne with two moles of HCI Reaction of ethene with Br₂ in H₂Oarrow_forwardNa, NH3 H3C-C=C-CH3 CH3 H3C° Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions .CH3 H-NH2 CH3 :NH2 H3C H3Carrow_forwardWhen an unsymmetrical alkene such as propene is treated with N-bromosuccinimide in aqueous dimethyl sulfoxide, the major product has the bromine atom bonded to the less highly substituted carbon atom. Is this Markovnikov or non-Markovnikov orientation? Show its reaction mechanism. OH Brz, H,O CH;CH=CH, CH;CHCH,Br What products would you expect from oxymercuration-demercuration of 1-hexene? Show the reaction mechanism. 1.Hg(AOc), H,0 CH;CH,CH,CH,CH=CH; 2. NaBH, hex-1-enearrow_forward
- Two substitution products result from the reaction between 3-chloro-3-methyl-1- butene with sodium acetate (CH3COO – Na +) in acetic acid under SN1. Identify the products.arrow_forwardAlkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions -X티 Hö: H-O -CH3 -CH3 H30*arrow_forwardC=CH H20, H2SO4 H9SO4 CH3 Alkynes do not react directly with aqueous acid as do alkenes, but will do so in the presence of mercury(II) sulfate as a Lewis acid catalyst. The reaction occurs with Markovnikov regiochemistry, so the OH group adds to the more highly substituted carbon and the H adds to the less highly substituted carbon. The initial product of the reaction is a vinyl alcohol, also called an enol. The enol immediately rearranges to a more stable ketone via tautomerization. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-OH HO: Hjö: C=CH c=CH Hö Hg Hgarrow_forward
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