(a)
Interpretation:
The synthesis is to be shown for the 4-chloro-3-nitrobenzoic acid from toluene.
Concept introduction:
Nitration: The formation of nitro group in a
Chromic Acid:
Chromic Acid (
(b)
Interpretation:
The reagent and condition is to be proposed for step 1.
(c)
Interpretation:
The mechanism is to be proposed for step 2.
Concept introduction:
Ipso substitution reaction: It is the one of the
(d)
Interpretation:
The reagent and condition is to be proposed for step 3.
Concept introduction:
Hydrogenolysis:
Metal catalyst gives the corresponding amine or alcohol.
Reductive amination reaction: Amination is the process by which an amine group is introduced into an organic molecule.
The conversion of Carbonyl group in to amine via imine intermediate is called reductive amination.
(e)
Interpretation:
The possible stereoisomer’s has to be shown if the product is chiral.
Concept introduction:
Isomer: A molecule having the same molecular formula but with different chemical structure is called isomer.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
Achiral:
A molecule is superimposable on its mirror image is called achiral molecule.
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Chapter 23 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Give mechanism asaparrow_forwardShow how to synthesize the following amines from the indicated starting materials byacylation–reduction.(a) N-butylpiperidine from piperidinearrow_forward(D)The best route to synthesise aromatic primary amines is by reduction of the corresponding nitro compounds. Draw the reaction scheme for the preparation of p-toluidine.arrow_forward
- In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forwardShow how to synthesize the following amines from the indicated starting materials byacylation–reduction. b) N-benzylaniline from anilinearrow_forwardPropose the synthesis for the following transformation.arrow_forward
- iv)Propose a mechanism (curved arrow formalism) for the reaction of the synthesis of a sulfonamide derivative from sulfathiazolearrow_forward(b) State the reagents needed to convert benzoic acid into the following compounds. (i) C6H§COCI (ii) C,H$CH2OH (iii) C6H$CONHCH3arrow_forwardPropose mechanisms consistent with the following reactions. (a) (b) (c) (d) (f) (breif Written explantion for each PLEASE) Propose mechanisms consistent with the following reactions. (a) HBr ROOR Br H₂SO4 (b) H₂O OH Br HBr Br (d) (c) CHBr Br NaOH Br Br (e) HCI CH3CH₂OH Br OCH2CH3 Br ED-8 CH2CH3 H- OH H+, H₂O (f) H OH CH3CH2 CH2CH3 CH2CH3 (continued)arrow_forward
- Show how to synthesize the following amines from the indicated starting materials byreductive amination.(a) benzylmethylamine from benzaldehydearrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardShow how to synthesize each of the following compounds using only a single nucleophilic aromatic substitution reaction. (a) NO, (b) (c) NO2 O,N ноarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning