Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 10, Problem 18P
Interpretation Introduction
Interpretation:
The mechanism for the given radical halogenation reaction is to be written.
Concept Introduction:
A free radical halogenation reaction is a type of reaction in which the replacement of hydrogen atom with a bromine atom in the moleculetakes place in the presence of UV light. It is a type of a halogenation reaction.
Molecules that have one unpaired electron are called free radicals.
A
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Write mechanism for the free radical Bromination of ethylbenzene. Include all possible resonance contributors.
Write the mechanism for the following reactions. Explain detail each steps of reactions.
Illustrate the resonance effect of the methoxy group -OCH3, on the structure of the benzene ring. Draw all the oissuvke resonance forms of methoxybenzene, including the hybrid Based on the structures, explain how the presence of the -OCH3 group affects: (i) the reactivity of the benzene ring towards electrophilic attack (ii) the orientation or point of attack of an incoming electrophilic reagent on the benzene ring.
Chapter 10 Solutions
Organic Chemistry
Ch. 10 - Prob. 1PPCh. 10 - Prob. 2PPCh. 10 - Practice Problem 10.3 How would the molecular ion...Ch. 10 - Prob. 4PPCh. 10 - Prob. 5PPCh. 10 - Prob. 6PPCh. 10 - Practice Problem 10.7 Chlorination reactions of...Ch. 10 - Prob. 8PPCh. 10 - Prob. 9PPCh. 10 - Prob. 10PP
Ch. 10 - Prob. 11PPCh. 10 - Practice Problem 10.12 Benzylic radicals, due to...Ch. 10 - Prob. 13PPCh. 10 - Practice Problem 10.14 Show how the following...Ch. 10 - Prob. 15PPCh. 10 - Prob. 16PPCh. 10 - Prob. 17PPCh. 10 - Prob. 18PCh. 10 - Explain the relative distribution of produces...Ch. 10 - 10.20 Which of the following compounds can be...Ch. 10 - Prob. 21PCh. 10 - Prob. 22PCh. 10 - Prob. 23PCh. 10 - Prob. 24PCh. 10 - 10.25 List in order of decreasing stability all of...Ch. 10 - Prob. 26PCh. 10 - Prob. 27PCh. 10 - Prob. 28PCh. 10 - Starting with the compound or compounds indicated...Ch. 10 - Prob. 30PCh. 10 - 10.31 Synthesize each of the following compounds...Ch. 10 - Synthesize each of die following compounds by...Ch. 10 - Prob. 33PCh. 10 - Prob. 34PCh. 10 - Prob. 36PCh. 10 - The halogen atom of an alkyl halide can be...Ch. 10 - Prob. 38PCh. 10 - Prob. 39PCh. 10 - Write a mechanism for the following reaction.Ch. 10 - 10.41 Hydrogen peroxide and ferrous sulfate react...Ch. 10 - Prob. 42PCh. 10 - If one were to try to draw the simplest Lewis...Ch. 10 - Prob. 1LGPCh. 10 - 2. (a) Propose a synthesis of 2-methoxypropene...
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
- The first step of the mechanism of this reaction involving vanillin is the formation of vanillin phenoxy radical by abstraction of the phenolic H atom. Just like some of the vitamins or BHT, vanillin can stabilize the radical through resonance. Draw all the neutral resonance structures of the vanillin radical. Select the structures which are NOT the resonance structures of the vanillin phenoxy radical from the list below. For clarity, all necessary hydrogens and lone pairs are implied. O Jo og J₂C-O 0 ICO sayarrow_forwardWrite mechanism of chain radical reaction of 2-methyl-2-butene in HBr and peroxide ROOR.arrow_forwardPlease answer the following: Cyclopropyl chloride can be prepared by the radical chlorination of cyclopropane, Write an overall equation for the reaction Suggest suitable reaction condition Write a stepwise mechanism for the radical halogenation reaction.arrow_forward
- Provide the curved-arrow mechanism to account for the following nucleophilic addition- elimination reaction. NaNarrow_forwardThe reaction is a nucleophilic substitution, A is OH- and B is an alkyl bromide. Give the reaction mechanism and explain your reasoning.arrow_forwardFill both dashes in the paragraph Compounds containing a phenol group may work as ANTIOXIDANTS to prevent free radical damage. This is accomplished when a free radical (or UV light) encounters a phenol group, turning the phenol group into a radical. However, contrary to typical radical behavior, the structure of the phenol radical can neutralize (or quench) the unpaired electron. Specifically, the phenol structure neutralizes (or quenches) the unpaired radical electron by doing the following: taking the electron and ---------. The correct name (or abbreviation) of an example compound (discussed in the lecture videos) containing a phenol group with antioxidant properties is: ---------.arrow_forward
- The high reactivity of alkyl halides can be explained in terms of nature of C-X bond which is highly polarized covalent bond due to large difference in the electronegativities of carbon and halogen atom. This polarity is responsible for the nucleophilic substitution reactions of alkyl halides which mostly occur by Swa and Swa mechanisms. Sy reaction is a two-step process and in the first step, R-X ionizes to give carbocation (slow process). In the second step, the nucleophile attacks the carbocation from either side to form the product (fast process). In Swi reaction, there can be racemization and inversion. Swi reaction is favored by heavy (bulky) groups on the carbon atom attached to halogens. i.e., R,C-X>R;CH-X>R-CH,X>CH,X. In Sna reaction, the strong nucleophile OH attacks from the opposite side of the chlorine atom to give an intermediate (transition state) which breaks to yield the product (alcohol) and leaving (X) group. The alcohol has a configuration opposite to that of the…arrow_forward(a) Why cyclohexene and cyclohexa-1,3-diene are expected to undergo addition reaction but benzene does not? Explain clearly. (b) Why is an electron-donating group to benzene activating and usually a/an ortho/para director?arrow_forwardElucidate the structure, hybridization, stability order and factors affecting the stability of an organic intermediate which is formed by the homolytic bond breaking.arrow_forward
- 11.; (a) Similar to alkanes, hydrogen gas can undergo radical bromination according to the reaction below. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal·mole', for H-Br is 88 kcal'mole and for H-H is 104 kcal'mole'. hv H-H + Br-Br 2 H-Br (b) Calculate the overall AH for the above propagation steps (show all work).arrow_forward46arrow_forwardIn the addition of bromine to cyclohexene in ether, which of the following statements are true? Choose all that apply. A) The reaction must occur in two steps for a trans product to be formed. B The reaction must be concerted for a trans product to be formed. (C) Br must add first as an electrophile and then bromide must add second as a nucleophile. D Bromide must add first as a nucleophile and then Br must add second as an electrophile.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 LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning