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
- Predict the major products of the following reaction. If it is possible, write all stereoisomers.arrow_forwardWrite a plausible mechanism for this transformation. Only two sequential pericyclic reactions are required.arrow_forwardThe following Diels-Alder reaction product is an intermediate in the synthesis of cholesterol. Provide the structure of the major product. Show stereochemistry when applicable. Hint: there are two possible dienophiles, which one is the better dienophile? Provide a brief explanation of your choice. CH,O.arrow_forward
- Give the correct order of the given compounds in order of decreasing reactivity towards electrophilic aromatic substitution.arrow_forwardCompounds P and Q can undergo a Diels-Alder reaction to form two regioisomeric products R and S as shown in Figure 5. OMe O C8H12O2 R C8H12O2 S Figure 5 Draw the chemical structures of regioisomeric compounds R and S. Using possible resonance contributors of P and Q predict which of the two regioisomers will be favoured in the reaction. Using curly arrows, draw the mechanism for the reaction of P and Q to form the dominant regioisomer you have predicted in your answer to part (ii) above.arrow_forwardComplete the following reactions, clearly indicating regio-and stereochemistry where applicable. In cases, where ortho-and para-products are formed, draw both.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_forwardA ketone undergoes acid-catalyzed bromination, acid-catalyzed chlorination, racemization, and acid-catalyzed deuterium exchange at the alpha-carbon. All of these reactions have similar rate constants. What does this tell you about the mechanisms of these reactions?arrow_forward
- A compound (C3H,NO) gives the following NMR data. In the box below please draw the structure of the compound. 'H-NMR: 2.06 ppm, s(3H); 7.01 ppm, t(1H); 7.30 ppm, m(2H); 7.59 ppm, d(2H); 9.90 ppm, s(1H) 13C-NMR: 168.14; 139.24; 128.511; 122.834; 118.90; 23.93 • 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.arrow_forward2) The Diels-Alder reaction, developed by German chemists Otto Diels and Kurt Alder (who received the Nobel Prize in 1950 for their discovery), has great synthetic importance due to the possibility of forming an unsaturated six-membered cycle without involving intermediates ionic. About the reaction, answer: (a) Indicate the reagents necessary for the synthesis of the following compounds, indicating who is the diene and who is the dienophile.arrow_forwardFor following substituted benzenes: [1] C6H5Br; [2] C6H5CN; [3] C6H5OCOCH3: Does the substituent activate or deactivate the benzene ring inelectrophilic aromatic substitution?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