a) Bromobenzene
Interpretation:
The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.
Concept introduction:
Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO3 and H2SO4. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.
To give:
The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.
Answer to Problem 47AP
The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.
Bromobenzene will react slower than benzene.
Explanation of Solution
Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.
The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.
Bromobenzene will react slower than benzene.
b) Benzonitrile
Interpretation:
The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.
Concept introduction:
Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO3 and H2SO4. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.
To give:
The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.
Answer to Problem 47AP
The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.
Benzonitrile will react slower than benzene.
Explanation of Solution
The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.
The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.
Benzonitrile will react slower than benzene.
c) Benzoic acid
Interpretation:
The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.
Concept introduction:
Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO3 and H2SO4. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.
To give:
The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.
Answer to Problem 47AP
The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.
Benzoic acid will react slower than benzene.
Explanation of Solution
The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.
The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.
Benzoic acid will react slower than benzene.
d) Nitrobenzene
Interpretation:
The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.
Concept introduction:
Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO3 and H2SO4. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.
To give:
The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.
Answer to Problem 47AP
The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.
Nitrobenzene will react slower than benzene.
Explanation of Solution
The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.
The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.
Nitrobenzene will react slower than benzene.
e) Benzenesulfonic acid
Interpretation:
The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.
Concept introduction:
Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO3 and H2SO4. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.
To give:
The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.
Answer to Problem 47AP
The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.
Benzenesulfonic acid will react slower than benzene.
Explanation of Solution
The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.
The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.
Benzenesulfonic acid will react slower than benzene.
f) Methoxybenzene
Interpretation:
The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.
Concept introduction:
Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO3 and H2SO4. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.
To give:
The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.
Answer to Problem 47AP
The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.
Methoxybenzene will react faster than benzene.
Explanation of Solution
The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.
The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.
Methoxybenzene will react faster than benzene.
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Chapter 16 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- Provide the missing reagents to complete the reactions below, if there is more than one step required, be sure to indicate appropriately.arrow_forwardArrange the compounds in order of INCREASING reactivity towards bromination. I. Toluene, Nitrobenzene, Iodobenzene, Acetanilide II. Phenol, Acetophenone, Anisole, Chlorobenzene III. Aniline, Benzaldehyde, Benzonitrile, Benzenesulfonic acidarrow_forwardWhat products would you would expect to obtain when the following compounds react with ozone and then with dimethylsulfide?arrow_forward
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Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning