
Concept explainers
Interpretation:
The equations for the preparation of each of the given compounds from benzene or toluene and any necessary organic or inorganic reagents are to be written.
Concept Introduction:
In electrophilic
When aromatic ring having two comparably activated positions then the substitution usually takes place at the less hindered position.
The reagent zinc amalgam and concentrated hydrochloric acid is use to convert a carbonyl group into methylene unit. This reaction is known as Clemmenson’s reduction.
In Friedel-Crafts acylation, acyl halides are used to yield aryl
In Friedel-Crafts
A mixture of nitric acid and sulfuric acid produces a nitronium ion which behaves as an electrophile in electrophilic aromatic substitution reactions.
Reagent bromine in acetic acid indicates bromination reaction.
Reagent sulfur trioxide in sulfuric acid indicates sulfonation reaction.
Oxidation of benzylic carbon atom is done using the

Answer to Problem 49P
Solution:
a) Reaction equations for the synthesis of isopropyl benzene from benzene is shown below:
b) Reaction equations for the synthesis of
c) Reaction equations for the synthesis of
d) Reaction equations for the synthesis of
e) Reaction equations for the synthesis of
f) Reaction equations for the synthesis of
g) Reaction equations for the synthesis of
h) Reaction equations for the synthesis of
i) Reaction equations for the synthesis of
j) Reaction equations for the synthesis of
k) Reaction equations for the synthesis of
l) Reaction equations for the synthesis of
m) Reaction equations for the synthesis of
n) Reaction equations for the synthesis of
Explanation of Solution
a) The structure for isopropyl benzene is:
Benzene undergoes Friedel-Crafts alkylation with isopropyl chloride with aluminum chloride to yield isopropyl benzene as shown below:
b) The structure of
In the above structure, the isopropyl substituents, isopropyl and sulfonic acid are para to each other.
Benzene undergoes Friedel-Crafts alkylation with isopropyl chloride with aluminum chloride to yield isopropyl benzene. In the second step, isopropyl benzene is treated with the solution of sulfur trioxide in sulfuric acid yields
Reaction equations for the synthesis of
c) The structure of
In the structure for the final product, the phenyl group and a bromine atom is attached to
d) The structure of
To get this product, toluene should be the starting compound that must be used. In the first step, toluene undergoes Friedel-Crafts alkylation with tertiary butyl chloride with aluminum chloride to yield tert-butyl toluene. In the second step, the tert-butyl toluene undergoes a nitration reaction to yield the product in which the nitro substituent is attached to the ortho position of the methyl group and meta position of the tertiary butyl group. Due to steric hindrance, the product in which the nitro group is attached at the ortho position of the tertiary butyl group is less favorable.
Reaction equations for the synthesis of
e) The structure for
To get this product, benzene should be the starting compound that must be used. In the first step, benzene undergoes Friedel-Crafts acylation with acyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
f) The structure of
In order to get this product, benzene should be the starting compound that must be used. In the first step, benzene undergoes chlorination reaction in presence of a Lewis acid such as aluminum chloride to yield chlorobenzene. In the second step, chlorobenzene undergoes Friedel-Crafts acylation with acyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
g) The structure for
On order to get this product, toluene should be the starting compound that must be used. In the first step, toluene undergoes Friedel-Crafts acylation with acyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
h) The structure for
To get this product, toluene should be the starting compound that must be used. In the first step, toluene undergoes Friedel-Crafts alkylation with ethyl chloride with aluminum chloride to yield
Reaction equations for the synthesis of
i) The structure for
To get this product, toluene should be the starting compound that must be used.
In the first step, toluene undergoes oxidation of benzylic carbon atom in toluene with
In the second step, benzoic acid undergoes a nitration reaction with a mixture of nitric acid and sulfuric acid giving
In the third step,
Reaction equations for the synthesis of
j) The structure for
To get the desired product, toluene should be the starting compound that must be used.
In the first step, toluene with nitric acid and sulfuric acid undergoes a nitration reaction giving
In the second step, benzoic acid undergoes bromination reaction in presence of a Lewis acid such as Iron (III) bromide to yield
In the third step,
Reaction equations for the synthesis of
k) The structure for
To get this product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with octanyl chloride with aluminum chloride.
In the second step, the carbonyl group is reduced in the presence of
Reaction equations for the synthesis of
l) The structure of
In order to get this product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with octenyl chloride with aluminum chloride.
In the second step, the carbonyl group is reduced to the hydroxyl group in the presence of
In the third step, the resulting alcohol is heated with sulfuric acid at high temperatures to yield
Reaction equations for the synthesis of
m) The structure of
To get this product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with octanyl chloride with aluminum chloride.
In the second step, the carbonyl group is reduced to the hydroxyl group in the presence of
In the third step, the resulting alcohol is heated with sulfuric acid at high temperatures to yield
In the fourth step,
Reaction equations for the synthesis of
n) The structure of
To get the required product, benzene should be the starting compound that must be used.
In the first step, benzene undergoes Friedel-Crafts acylation with tertiary butyl chloride with aluminum chloride giving tert-butyl toluene.
In the second step again, the tert-butyl toluene undergoes Friedel-Crafts acylation with tertiary butyl chloride with aluminum chloride giving
In the third step,
Reaction equations for the synthesis of
Want to see more full solutions like this?
Chapter 13 Solutions
Organic Chemistry - Standalone book
- give example for the following(by equation) a. Converting a water insoluble compound to a soluble one. b. Diazotization reaction form diazonium salt c. coupling reaction of a diazonium salt d. indacator properties of MO e. Diazotization ( diazonium salt of bromobenzene)arrow_forward2-Propanone and ethyllithium are mixed and subsequently acid hydrolyzed. Draw and name the structures of the products.arrow_forward(Methanesulfinyl)methane is reacted with NaH, and then with acetophenone. Draw and name the structures of the products.arrow_forward
- 3-Oxo-butanenitrile and (E)-2-butenal are mixed with sodium ethoxide in ethanol. Draw and name the structures of the products.arrow_forwardWhat is the reason of the following(use equations if possible) a.) In MO preperation through diazotization: Addition of sodium nitrite in acidfied solution in order to form diazonium salt b.) in MO experiment: addition of sodium hydroxide solution in the last step to isolate the product MO. What is the color of MO at low pH c.) In MO experiment: addition of sodium hydroxide solution in the last step to isolate the product MO. What is the color of MO at pH 4.5 d.) Avoiding not cooling down the reaction mixture when preparing the diazonium salt e.) Cbvcarrow_forwardA 0.552-g sample of an unknown acid was dissolved in water to a total volume of 20.0 mL. This sample was titrated with 0.1103 M KOH. The equivalence point occurred at 29.42 mL base added. The pH of the solution at 10.0 mL base added was 3.72. Determine the molar mass of the acid. Determine the Ka of the acid.arrow_forward
- As the lead product manager at OrganometALEKS Industries, you are trying to decide if the following reaction will its major product: 2,0° with a new C-C bond as If this reaction will work, draw the major organic product or products you would expect in the drawing aree below. If there's more than one major product, you can draw them in any arrangement you like. Be sure you use wedge and desh bonds if necessary, for example to distinguish between major products with different stereochemistry. If the major products of this reaction won't have a new C-C bond, just check the box under the drawing area and leave it blank.arrow_forwardwrite the mechanism of the nucleophilic acyl substitution reaction, please give an examplearrow_forwardThe compound in the figure is reacted with 10 n-butyllihium, 2° propanone, and 3º H2O. Draw and name the products obtained. SiMe3arrow_forward
- Caffeine (C8H10N4O2, pictured below) is a weak base. The pKb of caffeine is 10.4. What is the pH of a 0.0155 M solution of caffeine?arrow_forward2-Cyclopentyl-2-methyl-1,3-dioxolane is reacted with H₂SO₄. Draw and name the structures of the products.arrow_forwardIndicate the products of the reaction of 1-cyclohexyl-2,2-dimethylpropan-1-one with CH3CO3H (). Draw the structures of the compounds.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY





