Concept explainers
Interpretation:
The resonance structures for the intermediates from the reaction of an electrophile at the ortho, meta and para positions of nitrobenzene are to be drawn and among them the stable intermediates are to be indicated.
Concept introduction:
Resonance structures differ only in the positions of lone pair or π bonding electrons. The relative positions of atoms in different forms do not differ. Curved arrows are used to represent the shift of the electrons.
The stability of a resonance hybrid depends on the number of stable resonance forms that contribute to the resonance hybrid. The hybrid with large number of stable forms will be more stable.
To draw:
The resonance structures for the intermediates from the reaction of an electrophile at the ortho, meta and para positions of nitrobenzene and further to indicate the stable intermediates among them.
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Chapter 16 Solutions
ORGANIC CHEM.(LL)-W/OWL V2 >CUSTOM<
- Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.arrow_forwardOnce treated with HBr, which alkene is the most likely to undergo a carbocation rearrangement after the electrophilic addition step?arrow_forwardFill in the appropriate reagent or starting material in each of the following reactions.arrow_forward
- Select the electrophile from which the major product is formed.arrow_forwardIn the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?arrow_forwardFor each horizontal row of substituted benzenes, indicatea. the one that is the most reactive in an electrophilic aromatic substitution reaction.b. the one that is the least reactive in an electrophilic aromatic substitution reaction.c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.arrow_forward
- Assume that attached starting materials can be converted to an epoxide by this reaction. Draw the product formed (including stereochemistry) from each starting material. Why might some of these reactions be more difficult than others in yielding nucleophilic substitution products?arrow_forwardDraw resonance structures of anisole or the intermediate in the above reaction to demonstrate why the methoxy group is an o,p-directorarrow_forwardWhy does increasing alkyl substitution increase the rate of an E2 reaction?arrow_forward
- Which of the following is a correct statement regarding electrophilic aromatic substitution? A. Many suitable electrophiles are unreactive and can be stored for long periods of time prior to use. B. The carbocation intermediate will lose a proton to regain aromaticity, usually from a position other than the site of the electrophilic attack. C. Formation of the carbocation intermediate has a high activation barrier due to loss of aromaticity. D. Reformation of the aromatic ring has a low activation barrier and therefore occurs slowly. E. The carbocation intermediate has several resonance structures and is negatively charged.arrow_forwardDefine the Stereochemistry of the E2 Reaction ?arrow_forwardWrite the mechanism of this pericyclic reactionarrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning