Concept explainers
a) Chlorobenzene, o-dichlorobenzene and benzene
Interpretation:
The compounds chlorobenzene, o-dichlorobenzene and benzene are to be ranked according to their reactivity towards electrophilic substitution.
Concept introduction:
To rank:
The compounds chlorobenzene, o-dichlorobenzene and benzene according to their reactivity towards electrophilic substitution.
b) p-bromonitrobenzene, nitrobenzene, phenol
Interpretation:
The compounds p-bromonitrobenzene, nitrobenzene and phenol are to be ranked according to their reactivity towards electrophilic substitution.
Concept introduction:
Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.
To rank:
The compounds p-bromonitrobenzene, nitrobenzene and phenol according to their reactivity towards electrophilic substitution.
c) Fluorobenzene, benzaldehyde, o-xylene
Interpretation:
The compounds fluorobenzene, benzaldehyde and o-xylene are to be ranked according to their reactivity towards electrophilic substitution.
Concept introduction:
Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.
To rank:
The compounds fluorobenzene, benzaldehyde and o-xylene according to their reactivity towards electrophilic substitution.
d) Benzonitrile, p-methylbenzonitrile, p-methoxybenzonitrile
Interpretation:
The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile are to be ranked according to their reactivity towards electrophilic substitution.
Concept introduction:
Aromatic compounds that contain an ortho and para directing substituent groups (except halogens) are more reactive than benzene and that contain meta directing substituent groups are less reactive than benzene. Halogens are ortho & para directing yet deactivating groups. Hence the halogen substituted benzenes are less reactive than benzene.
To rank:
The compounds benzonitrile, p-methylbenzonitrile and p-methoxybenzonitrile according to their reactivity towards electrophilic substitution.
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Chapter 16 Solutions
Organic Chemistry
- Rank the compounds in each group according to their reactivity toward electrophilic substitution: (a) Chlorobenzene, o-dichlorobenzene, benzene (b) p-Bromonitrobenzene, nitrobenzene, phenol (c) Fluorobenzene, benzaldehyde, o-dimethylbenzenearrow_forward(a) How will you convert:(i) Benzene to acetophenone (ii) Propanone to 2-Methylpropan-2-ol(b) Give reasons :(i) Electrophilic substitution in benzoic acid takes place at meta position.(ii) Carboxylic acids are higher boiling liquids than aldehydes, ketones and alcohols of comparable molecular masses.(iii) Propanal is more reactive than propanone in nucleophilic addition reactions.arrow_forwardWrite the structure of the major organic product formed in the reaction of 1-pentene with each of the following: (a) Hydrogen chloride (b) Dilute sulfuric acid (c) Diborane in diglyme, followed by basic hydrogen peroxide (d) Bromine in carbon tetrachloride (e) Bromine in water (f) Peroxyacetic acid (g) Ozone (h) Product of part (g) treated with zinc and water (i) Product of part (g) treated with dimethyl sulfide (CH3)2Sarrow_forward
- Electrophilic aromatic substitution usually occurs at the 1-position of naphthalene, also called the a position. Predict themajor products of the reactions of naphthalene with the following reagents.(a) HNO3, H2SO4 (b) Br2, FeBr3 (c) CH3CH2COCl, AlCl3(d) isobutylene and HFarrow_forward(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.arrow_forwardDescribe how would you distinguish the following pairs, (a) Benzene and cyclohexane (b) Phenol and toluene (c) Phenol and benzoic acidarrow_forward
- 11:43 Q1. (a) (c) (d) (b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with ethanolic potassium hydroxide. (i) Explain what is meant by the term stereoisomers. Library Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH₂ Name of mechanism Mechanism (ii) Draw the structures and give the names of the two stereoisomers of but-2-ene. Stereoisomer 1 Name (iii) Name this type of stereoisomerism. Select Name Stereoisomer 2 When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide, 2-methylpropan-2-ol is formed as shown by the following equation. CH3 H₂C-C-CH3 + KOH Br Page 2 of 14 CH3 H3C-C-CH3 + KBr ОН State the role of the hydroxide ions in this reaction. Write an equation for the reaction that occurs when CH3CH₂CH₂CH₂Br reacts with an excess of ammonia. Name the organic product of this reaction. Equation Name of product 9,284 Photos, 1,166 Videos For You…arrow_forward(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enalarrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forward
- The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?arrow_forwardNucleophilic aromatic substitution provides one of the common methods for making phenols. Show how you would synthesize the following phenols, using benzene or toluene as your aromatic starting material, and explain why mixtures of products would be obtained in some cases.(a) p-nitrophenol (b) 2,4,6-tribromophenol (c) p-chlorophenolarrow_forwardBorazole, B3N3H6, is an unusually stable cyclic compound. Propose a structure forborazole, and explain why it is aromatic.arrow_forward
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