Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 7.SE, Problem 24VC
The following carbocation is an intermediate in the electrophilic addition reaction of HCl with two different
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H3C
CH3
H3C
NA C→XT
Br
Br₂
CH₂Cl₂
H3C
Electrophilic addition of bromine, Br₂, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic
intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH₂Cl₂.
CH3
Br
In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion
to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the
bromonium ion so that a product with anti stereochemistry is formed.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
Br
CH3
H3C
CH3
Shown below is a carbocation intermediate in an electrophilic addition reaction of HCl with an alkene.
For the conformation shown, select each hydrogen whose bond to carbon is aligned for effective hyperconjugation with the vacant p orbital on the positively charged
carbon. Each adjacent carbon will have only one C-H bond so aligned.
• Gray = C; white = H; red = 0; blue = N; dark green = Cl; brown =Br; light green =F; purple = I; yellow = S; orange = P.
• Double click to select atoms.
• You can zoom in and out using the mouse scroll wheel (or pinch to zoom on touch screens).
Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.
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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- Alcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardDefine the Mechanism of the Radical Addition of HBr to an Alkene ?arrow_forward
- CH3 CH3 Br- Br2 .CH3 CH2Cl2 CH3 H3C H3C Br Electrophilic addition of bromine, Brɔ, to alkenes yields a 1,2-dibromoalkane. The reaction proceeds through a cyclic intermediate known as a bromonium ion. The reaction occurs in an anhydrous solvent such as CH,Cl,. In the second step of the reaction, bromide is the nucleophile and attacks at one of the carbons of the bromonium ion to yield the product. Due to steric clashes, the bromide ion always attacks the carbon from the opposite face of the bromonium ion so that a product with anti stereochemistry is formed. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 CH3 CH3 H3C H3C :Br: :Br:arrow_forwardDraw an approximate reaction-energy diagram showing the curves for the two possible pathways for ionic addition of HBr to 1-methylcyclohexene. (a) Formation of the major product, 1-bromo-1-methylcyclohexane, and (b) formation of the minor product, 1-bromo-2-methylcyclohexane. Point out how these curves show that 1-bromo-1-methylcyclohexane should be formed fasterarrow_forward2. The following carbocation is generated as an intermediate in the addition of H-Br to an alkene. Draw the structure of all possible alkenes that could have formed this intermediate.arrow_forward
- The compound below is treated with chlorine in the presence of light. H3C CH3 H3C° `CH2CH3 Draw the structure for the organic radical species produced by reaction of the compound with a chlorine atom. Assume reaction occurs at the weakest C-H bond. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms.arrow_forward5B 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 CH3 H3C-C H -Br CH3 EtOHarrow_forwardShown below is a carbocation intermediate in an electrophilic addition reaction of HCl with two different alkenes. Draw structural formulas for both of the alkenes.arrow_forward
- Draw the bond-line (skeletal) structure of the compound with molecular formula C₂H₁3Br that gives the following alkene as the exclusive product of E2 elimination. Click and drag to start drawing a structure. C X C Ś c+arrow_forwardUnder certain reaction conditions, 2,3-dibromobutane reacts with two equivalents of base to give three products, each of which contains two new p bonds. Product A has two sp hybridized carbon atoms, product B has one sp hybridized carbon atom, and product C has none. What are the structures of A, B, and C?arrow_forwardThe two alkenes below react with HI at different rates. CH3CH=CHCH3 and CH₂=CH₂ Draw the structural formula of the MAJOR product formed by the alkene having the HIGHER reaction rate. • 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. TAYY [ ] در ChemDoodle Ⓡarrow_forward
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