
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
Organic Chemistry
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- Determine the structures of the missing organic molecules in the following reaction: + H₂O +H OH O OH +H OH X Note: Molecules that share the same letter have the exact same structure. In the drawing area below, draw the skeletal ("line") structure of the missing organic molecule X. Click and drag to start drawing a structure.arrow_forwardIdentify the missing organic reactant in the following reaction: x + x O OH H* + ☑- X H+ O O Х Note: This chemical equation only focuses on the important organic molecules in the reaction. Additional inorganic or small-molecule reactants or products (like H₂O) are not shown. In the drawing area below, draw the skeletal ("line") structure of the missing organic reactant X. Click and drag to start drawing a structure. Carrow_forwardCH3O OH OH O hemiacetal O acetal O neither O 0 O hemiacetal acetal neither OH hemiacetal O acetal O neither CH2 O-CH2-CH3 CH3-C-OH O hemiacetal O acetal CH3-CH2-CH2-0-c-O-CH2-CH2-CH3 O neither HO-CH2 ? 000 Ar Barrow_forward
- What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 2 2. n-BuLi 3 Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Explanation Check Click and drag to start drawing a structure.arrow_forwardPredict the products of this organic reaction: NaBH3CN + NH2 ? H+ Click and drag to start drawing a structure. ×arrow_forwardPredict the organic products that form in the reaction below: + OH +H H+ ➤ ☑ X - Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Click and drag to start drawing a structure. Garrow_forward
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