a)
Interpretation:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution is to be stated.
Concept introduction:
In
To state:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution.
b)
Interpretation:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions both -NH- and halogens are ortho and para directing as they stabilize the carbocation intermediates for these attacks. If two alternate options exist, the electrophile will enter into the more activated ring. The orientation of the incoming electrophile will be decided by the stronger of the two substituent groups already present.
To state:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution.
c)
Interpretation:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions, both aryl and alkyl are ortho and para directing as they stabilize the carbocation intermediates for these attacks. If two alternate options exist, the electrophile will enter into the more activated ring. The orientation of the incoming electrophile will be decided by the stronger of the two substituent groups already present.
To state:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution.
d)
Interpretation:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution is to be stated.
Concept introduction:
In aromatic electrophilic substitution reactions –C=O group is meta directing while halogens are ortho and para directing. If two alternate options exist the electrophile will enter into the more activated ring. The orientation of the incoming electrophile will be decided by the stronger of the two substituent groups already present.
To state:
The position and the ring in which the compound shown is expected to undergo electrophilic substitution.
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Chapter 16 Solutions
Organic Chemistry
- Establish the reaction and propose a mechanism to obtain the following compound from the Gringnard reaction. CH,CH,arrow_forwardThe free-radical bromination of the following compound introduces bromine primarily at the benzylic position next to the aromatic ring. If the reaction stops at the monobromination stage, two stereoisomers result. Draw the two stereoisomers that result from monobromination at the benzylic position.arrow_forwardWrite a plausible mechanism for this transformation. Only two sequential pericyclic reactions are required.arrow_forward
- Give the correct order of the given compounds in order of decreasing reactivity towards electrophilic aromatic substitution.arrow_forwardp-Fluoronitrobenzene is more reactive toward hydroxide ion than is p-chloronitrobenzene. What does this tell you about the rate-determining step for nucleophilic aromatic substitution?arrow_forward(b) Predict the major product (or products) formed when each of the following compounds 11- 14 reacts with a mixture of concentrated HNO3 and H2SO4. CO2H HN CO2H CI 11 12 13 14 (c) Pick one of the reactions under (b) and write the mechanism of the electrophilic aromatic substitution in detail (generation of the attacking electrophile is not required).arrow_forward
- Starting with Benzene (or naphthalene or biphenyl) Show a sequence of 3 electrophilic aromatic substitution reactions. And the intermediates and products Each EAS reaction must introduce a different group on the ringarrow_forwardWhich of the following compounds could be protonated without destroying its aromaticity?arrow_forwardBS21008 Organic Chemistry for the Life Sciences Assignment Week 7 Bearing in mind Huckel's rule, determine whether each of the heterocycles involved in the following acid-base equilibria is aromatic or not (show your working). Use your findings to explain which of the nitrogen atoms in the indazole ring is more basic, i.e. which would be the product of indazole protonation, compound A or compound B? + H* + H* N: - H* - H* H CH3 CH3 CH3 A 1-methyl-1H-indazolearrow_forward
- Treatment of a cyclic ketone with diazomethane is a method for accomplishing a ring-expansion reaction. The reaction involves the initial nucleophilic attack by diazomethane on the carbonyl carbon to form a tetrahedral intermediate. Collapse of this intermediate is accompanied by bond migration and loss of N,. For example, treatment of cyclohexanone with diazomethane yields cycloheptanone. CH2N2, ether + N2 Draw the structure of the organic product(s) of the ring expansion of this compound: • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • Do not include lone pairs in your answer. They will not be considered in the grading. • Draw one structure per sketcher Add additional ketchers usina the dron down menu in the bottom right co Previous Nextarrow_forwardWhich of the conditions below would provide the following transformation?arrow_forwardWhich of the reaction conditions could afford the following transformation?arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning