(a)
Interpretation:
The preparation method of benzyl methyl ether from toluene is to be stated.
Concept introduction:
Cyclic
Answer to Problem 17.28AP
The preparation method of benzyl methyl ether from toluene is shown below.
Explanation of Solution
For preparing benzyl methyl ether from toluene, toluene is first brominated.
For bromination of toluene,
The corresponding reaction sequences are shown below.
Figure 1
The preparation method of benzyl methyl ether from toluene is shown in Figure 1.
(b)
Interpretation:
The preparation method of
Concept introduction:
Cyclic alkenes on reaction with N-Bromosuccinimide (NBS) forms allyl or benzyl bromide, that is, bromine is substituted at the allylic or benzylic position. NBS is a rich source of free radical of
Answer to Problem 17.28AP
The preparation method of
Explanation of Solution
In given reaction, toluene is first brominated with NBS (N-bromosuccinamide). Brominated benzyl reacts with Grignard reagent and
The corresponding reaction sequences to obtain the desired product are shown below.
Figure 2
The preparation method of
(c)
Interpretation:
The preparation method of
Concept introduction:
The Lindlar’s catalyst is composed of
Answer to Problem 17.28AP
The preparation method of
Explanation of Solution
The addition of
The corresponding reaction sequences to obtain the desired product are shown below.
Figure 3
The preparation method of
(d)
Interpretation:
The preparation method of given compound from cyclopentene is to be stated.
Concept introduction:
Cyclic alkenes on reaction with N-Bromosuccinimide (NBS) forms allyl or benzyl bromide, that is, bromine is substituted at the allylic or benzylic position. NBS is a rich source of free radical of
Answer to Problem 17.28AP
The preparation method of given compound from cyclopentene is shown below.
Explanation of Solution
Cyclopentene is first brominated and then on treatment with Grignard reagent and epoxide it gives corresponding alkyl alcohol. This alkyl alcohol is oxidized with mild reagent PCC to convert it into
The corresponding reaction sequences to obtain the desired product are shown below.
Figure 4
The preparation method of given compound from cyclopentene is shown in Figure 4.
(e)
Interpretation:
The preparation method of
Concept introduction:
The
Answer to Problem 17.28AP
The preparation method of
Explanation of Solution
Cumene has to be oxidized first and then its nitration is done to get the required product
Alkyl group is oxidized to gives benzoic acid. This benzoic acid is nitrated with
The corresponding reaction sequences to obtain the desired product are shown below.
Figure 5
The preparation method of
(f)
Interpretation:
The preparation method of para-nitro benzoic acid from cumene (isopropyl benzene) is to be stated.
Concept introduction:
The chemical reaction in which an electrophile group is replaced by another functional group is known as the electrophilic substitution reaction. When the electrophilic substitution happens on an aromatic ring such as benzene then the reaction is known as electrophilic aromatic substitution.
Answer to Problem 17.28AP
The preparation method of para-nitro benzoic acid from cumene (isopropyl benzene) is shown below.
Explanation of Solution
As alkyl group is ortho and para directing, so, both the derivatives are formed. The reaction of cumene with nitric acid results in the formation of ortho and para nitro-cumene. The para nitro cumene is further oxidized to p-nitro benzoic acid with potassium permangnate.
The corresponding reaction sequences to obtain the desired product are shown below.
Figure 6
The preparation method of para-nitro benzoic acid from cumene (isopropyl benzene) is shown in Figure 6.
(g)
Interpretation:
The preparation method of
Concept introduction:
Cyclic alkenes on reaction with N-Bromosuccinimide (NBS) forms allyl or benzyl bromide, that is, bromine is substituted at the allylic or benzylic position. NBS is a rich source of free radical of
Answer to Problem 17.28AP
The preparation method of
Explanation of Solution
In the given reaction, at first, the substrate,
The corresponding reaction sequences to obtain the desired product are shown below.
Figure 7
The preparation method of
(h)
Interpretation:
The preparation of given compound from cyclopentenol is to be given.
Concept introduction:
The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as a substitution reaction. In a nucleophilic substitution reaction, nucleophile takes the position of leaving the group by attacking the electron-deficient carbon atom.
Answer to Problem 17.28AP
The preparation of given compound from cyclopentenol is shown below.
Explanation of Solution
The given reaction is a nucleophilic substitution reaction. The nucleophile attacks to replace the
This is a single step substitution nucleophile reaction as shown below.
Figure 8
In this reaction, the stereochemistry of molecule changes as from one side the group is leaving and upon other side of the molecule, nucleophile attacks.
The preparation of given compound from cyclopentenol is shown in Figure 8.
Want to see more full solutions like this?
Chapter 17 Solutions
Organic Chemistry
- (a) Give the products of the phosphoric acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Label the three products with major, minor, and trace amounts. OH H3PO4, heat (b) Describe the rule that is applied in the acid-catalyzed dehydration of 2-methylcyclohex-3- enol. Explain your answer based on the products formed.arrow_forward(a) benzene can potentially react with Lewis acid to form new carbon-carbon bond. Propose the starting material and stepwise mechanism to produce new chemical structure which consists of a formula molecule of C11H16.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
- (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_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(a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) Ph Ph 8*8 Ph THF A 1 Santande B H₂SO4 100 °C 3 OH Using curly arrows, provide full mechanistic details accounting how methylenecyclohexane 2 was synthesised according to both Methods A and B.arrow_forward
- (a) Give chemical tests to distinguish between the following pairs of compounds :(i) Pentan-2-ol and Pentan-3-ol (ii) Methanol and Phenol(b) o-nitro phenol is more acidic than o-methoxy phenol. Explain why.arrow_forwardExplain the following behaviours :(i) Alcohols are more soluble in water than the hydrocarbons of comparable molecular masses.(ii) Ortho-nitrophenol is more acidic than ortho-methoxyphenol.arrow_forwardStarting with 2-methylpropene, outline a synthesis of (a) (CH3)3COH (b) (CH3)2C(OH)CH2Brarrow_forward
- (a) Tsomane and Nyiko were given a task of synthesising methylenecyclohexane 2. After a brief discussion with each other, Tsomane proposed Method A to synthesise 2 from cyclohexanone 1 while Nyiko proposed Method B that started from hydroxymethylcyclohexane 3. Each student believed that their proposed method is better than the other. (Scheme below) (1) 1 Ph THF A Ph Ph B H₂SO4 100 °C 3 OH What is the name of the reaction that is followed by reaction Method A?arrow_forward(3) (a) Predict the product of the reaction between benzoyl chloride and any one of the following reagents. (i) Li(Et),Cu in ether (ii) BuMgBr in ether, then H3O+arrow_forwardFuran undergoes electrophilic aromatic substitution more readily than benzene; mild reagents and conditions are sufficient.For example, furan reacts with bromine to give 2-bromofuran.(a) Propose mechanisms for the bromination of furan at the 2-position and at the 3-position. Draw the resonance forms ofeach sigma complex, and compare their stabilities.(b) Explain why furan undergoes bromination (and other electrophilic aromatic substitutions) primarily at the 2-position.O Br O123furan 2-bromofuranarrow_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