Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
thumb_up100%
Chapter 10.SE, Problem 36AP
Interpretation Introduction
Interpretation:
The resonance structures are to be drawn for the benzyl radical, an intermediate formed in the NBS bromination of toluene.
Concept introduction:
Resonance forms differ only in the placement of their π bonding and lone-pair of electrons. The positions of atoms do not differ in different structures. The movement of electrons from one resaonance structure to other is indicated with curved arrows.
To draw:
The resonance structures for the benzyl radical, an intermediate formed in the NBS bromination of toluene.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
10) Synthesis: Make the following products from a suitable cyclic alkene starting material. Look
at the functional group PATTERN present in the molecule, including stereochemistry.
♡
Br
Br
An important step in one synthesis of carboxylic acids is the deprotonation of diethyl malonate and its alkyl-substituted
derivative:
Base
CH;CH2O
OCH,CH3
CH;CH,0
OCH2CH3
H2
Diethyl malonate
Base
CH;CH,0
°C
`OCH,CH3
CH;CH,O
OCH,CH3
R
Alkyl substituted diethyl malonate
NaOH can deprotonate diethyl malonate effectively, but NaOC(CH3)3 is typically used to deprotonate the alkyl-substituted
derivative. Explain why.
5B
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
EtOH
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
- Draw the structures of all monobromo derivatives of 2-methylpentane, C6H13Br, which have the bromine on a primary carbon.arrow_forward2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.arrow_forwardPropose a structure for an aromatic hydrocarbon, C,H12, that can form two CH11C1 products on substitution of a hydrogen on the aromatic ring with chlorine.arrow_forward
- A hydrocarbon C5H12 gives only one mono-chlorination product. Identify the hydrocarbon.arrow_forwardIn the reaction of ethylene with H20O in the presence of sulfuric acid,which one adds across the double bond first? *arrow_forwardAll electrophilic aromatic substitution reactions occur via a two-step mechanism: addition of the electrophile to form a resonance-stabilized carbocation, followed by deprotonation by a base. In the step shown below, loss of a proton to form the substitution product was drawn using the resonance structure with the + 1 formal charge at the ortho position to the carbon bonded to the electrophile. Redraw the step shown with the other two resonance structures and use curved arrows to show how these other two resonance structures can be converted to the substitution product by removal of a proton with the base shown. Part: 0/2 Part 1 of 2 H :CI-AICI, Draw the mechanism that generates the final substitution product with the +1 formal charge at the para position. Cl HC1 AICI3arrow_forward
- 4.) HX is used as a reagent in the reaction below. „NH2 он + HX + :NEN: + A. What functional-group transformation occurs in this reaction?arrow_forwardA certain hydrocarbon had the molecular formula C18H30 and contained two triple bonds. Ozonolysis gave CH₂(CH₂)CO₂H and HO₂CCH₂CH₂CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure.arrow_forward8. a) b) Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the following reactions. OEt COOH CH3 CH; 0 OH 1. LiAlH4, ether 2. HO OH ند (CH3COO NaOH, H₂O 5 CH 3 Clarrow_forward
- 3. Please draw the most important (stable) resonance form of the carbonation that mediates the following reaction: OH H3O+ O 4. Draw the structure of the alkene isomer (with the molecular formula of C5H10) that is most reactive one in the addition reaction with Br₂.arrow_forward2 methylbutene react with Hbr to givearrow_forward13-57 Benzene, as we have seen in this chapter, is the simplest aromatic compound. Pyidine is an analog of benzene in which a CH group is replaced by a nitrogenarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning