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.
Trending nowThis is a popular solution!
Chapter 16 Solutions
Organic Chemistry
- (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_forwardConsider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?arrow_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_forwardProvide reagentsarrow_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
- Starting from bromoethane, the formation of which of the following compound requires more than one step of reaction? 2 (a) Methoxyethane (b) Ethanol (c) Ethanoic acid (d) Ethenearrow_forwardThe endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rainforests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resulting conjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.arrow_forwardThe endiandric acids comprise a group of unsaturated carboxylic acids isolated from a tree that grows in the rain forests of eastern Australia. The methyl esters of endiandric acids D and E have been prepared from polyene Y by a series of two successive electrocyclic reactions: thermal ring closure of the conjugated tetraene followed by ring closure of the resultingconjugated triene. (a) Draw the structures (including stereochemistry) of the methyl esters of endiandric acids D and E. (b) The methyl ester of endiandric acid E undergoes an intramolecular [4 + 2] cycloaddition to form the methyl ester of endiandric acid A. Propose a possible structure for endiandric acid A.arrow_forward
- (c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.arrow_forwardCiprofloxacin is a member of the fluoroquinolone class of antibiotics.(a) Which of its rings are aromatic?arrow_forward(a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the product formed. (b) Predict the product(s) will be formed from the following reactions: (i) Bromination of p-methylbenzoic acid (ii) Sulphonation of m-bromoanisole (iii) Friedel-craft acylation of o-bromonitrobenzenearrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning