Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 10.SE, Problem 45AP
Interpretation Introduction
Interpretation:
Given that tertiary
Concept introduction:
The stability of free radicals is in the order benzyl > allyl > tertiary > secondary > primary > mehyl. The benzyl and allyl radicals are stabilized by resonance while tertiary, secondary and primary radicals are stabilized by hyperconjucation.
To explain:
Among (CH3)3CBr and H2C=CH C(CH3)2Br which will react faster.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
a. Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement. b. Would both alkenes form the same alkyl halide if DBr were used instead of HBr? (D is an isotope of H, so D+ reacts like H+.)
Identify two alkenes that react with HBr to form 1-bromo-1-methylcyclohexane without undergoing a carbocation rearrangement.
draw the two possible carbocations that can form when this alkene reacts with a strong acid (such as HBr or H3O+). of the two structures you drew, circle the more stable carbocation
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
Knowledge Booster
Learn more about
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
- In light of the fact that tertiary alkyl halides undergo spontaneous dissociation to yield a carbocation plus halide ion (see Problem 10-45), propose a mechanism for the following reaction.arrow_forwardwhat is the expected major product of HBr addition to the alkene shown below? Show the mechanismarrow_forwardWhat are ALL of the products of buta-1,3-diene and bromine water? I know how to get to the major product (bromine and OH both to the left of the double bond) but don't know how to get to the minor product (bromine to the left, OH to the right)?arrow_forward
- For each alkane, which mono brominated derivatives could you form in good yield by free-radical bromination?(a) cyclopentane (b) methylcyclopentane(c) 2-methylpentane (d) 2,2,3,3-tetramethylbutanearrow_forwardWhich alkenes shown below undergo rearrangement upon addition of HX?arrow_forwardThe addition of a halogen to an alkene results in a ___________ with __________ addition. tertiary halide, syn geminal dihalide, anti vicinal dihalide, anti primary halide, syn 1,1,2,2-tetrahalide, synarrow_forward
- Which reaction would you expect to be faster, addition of HBr to cyclohexene or to 1-methylcyclohexane? Explain.arrow_forwardWith POCl3, If dehydration is not possible, a substitution can occur instead. Provide a mechanism to account for the formation of this compound. Be sure that your steps are as simple as possible and conform to the conditions of the reaction.arrow_forward1,3- Butadiene undergoes an electrophilic addition with Hbr. Complete the steps in the mechanism to produce the product.arrow_forward
- best condition for the reaction (1r,2s)-1 bromo-2methylcyclohexane->(s)3-methylcyclohex-1enearrow_forwardReaction of 2-methyl-2-butene (above) with HBr might, in principle, lead to a mixture of two alkyl bromide addition products. Draw these two alkyl bromides.arrow_forwardDraw the four resonance structures formed during bromination of methoxybenzene, CH3OC6H5, with Br2/FeBr3 to give para-bromomethoxybenzene and then circle the most stable resonance form.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning