
Concept explainers
Interpretation:
Given that the substitution reaction of toluene with Br2 can, in principle, lead to the formation of three isomeric bromotoluene products. In practice, however, only o- and p-bromotoluene are formed in substantial amounts. The meta isomer is not formed. The structures of three possible carbocation intermediates are to be drawn and the predominance of ortho and para products over the meta product is to be explained.
Concept introduction:
When a monosubstituted benzene is subjected to electrophilic substitution reaction, the electrophile in principle can get substituted in any of the three positions, ortho, meta and para. Which isomer will be formed predominantly depends on the stability of the allylic intermediate formed by the attack of the electrophile on the benzene ring. The more stable intermediate will yield the products.
To draw:
The structures of three possible carbocation intermediates formed during the substitution reaction of toluene that leads to the formation of o-, p- and m-bromotoluenes.
To explain:
The observation when toluene reacts with bromine the ortho and para products are formed predominantly than the meta product.

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Chapter 15 Solutions
Organic Chemistry - With Access (Custom)
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- A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?arrow_forwardWhere are the chiral centers in this molecule? Also is this compound meso yes or no?arrow_forwardPLEASE HELP! URGENT!arrow_forward
- Where are the chiral centers in this molecule? Also is this compound meso yes or no?arrow_forwardA mixture of C7H12O2, C9H9OCl, biphenyl and acetone was put together in a gas chromatography tube. Please decide from the GC resutls which correspond to the peak for C7,C9 and biphenyl and explain the reasoning based on GC results. Eliminate unnecessary peaks from Gas Chromatography results.arrow_forwardIs the molecule chiral, meso, or achiral? CI .CH3 H₂C CIarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning

