Concept explainers
Interpretation:
The product obtained in each base-catalyzed Michael reaction is to be predicted and the mechanism for all the steps is to be shown.
Concept introduction:
Electrophiles are electron deficient species that have positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.
Nucleophiles are electron rich species that have negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.
Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.
Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.
Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.
Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.
In the Michael reaction, the conjugate addition of enolate to
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Organic Chemistry
- Syntheses of each of the following compounds have been reported in the chemical literature. Using the indicated starting material and any necessary organic or inorganic reagents, describe short sequences of reactions that would be appropriate for each transformation. (a) 1,1,5-Trimethylcyclononane from 5,5-dimethylcyclononanonearrow_forwardDeduce the structures of compounds A and B, two of the major components of jasmine oil, from the given data. Compound A: C9H10O2; IR absorptions at 3091–2895 and 1743 cm-1; 1H NMR signals at 2.06 (singlet, 3 H), 5.08 (singlet, 2 H), and 7.33 (broad singlet, 5 H) ppm. Compound B: C14H12O2; IR absorptions at 3091–2953 and 1718 cm-1; 1H NMR signals at 5.35 (singlet, 2 H) and 7.26–8.15 (multiplets, 10 H) ppm.arrow_forwardWolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.arrow_forward
- Identify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forwardb) Compound A, C;H14 undergo hydration to form B which is optically active. Compound A reacts with cold alkaline potassium manganate (VII) to form C. Ozonolysis of compound A forms methanal and 3,3-dimethylbutanal. Deduce structure A, B, and C.arrow_forwardGive reasons for the following: (i) Benzyl chloride is highly reactive towards the SN1 reaction. (ii) 2-bromobutane is optically active but 1-bromobutane is optically inactive. (iii) Electrophilic reactions in haloarenes occur slowly.arrow_forward
- 2. (a) Ozonolysis of compound A, C,H12 gave two products B and C. Further analysis of these two compounds of B and C, showed positive results with 2,4-dinitrophenylhydrazine. Compound B reacts with Tollens' reagent while compound C does not indicate any positive result to the same reagent. However, both B and C gave same positive results with iodoform test. (i) By writing all the chemical equations involved, identify A, B and C.arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?arrow_forward(c) In the reaction scheme below, compound D is a bicyclic aromatic heterocycle that is prepared via intermediate C. Compound D has a molecular formula of C10H11N and reacts with acetone to form E, which has a molecular formula of C23H26N2. Draw the structures of C, D and E and provide mechanisms for their formation. N CH₂CH3 + Br- CH3 C NaOH (aq) D H3C CH3 H₂SO4 (aq) Earrow_forward
- Give reasons : (i) 2, 4-Dinitro chlorobenzene is much more reactive than chlorobenzene towards hydrolysis reaction with NaOH. (ii) Grignard reagent should be prepared under anhydrous conditions. (iii) The dipole moment of chlorobenzene is lower than that of cyclohexyl chloride. (vi) Neopentyl bromide undergoes nucleophilic substitution reactions very slowly (v) Vinyl chloride is unreactive in nucleophilic substitution reaction. (vi) An optically inactive product is obtained after the hydrolysis of optically active 2- bromobutane.arrow_forwardIn 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_forward7B. (2 reactions (should clearly indicate the stereochemistry). Draw the structure of the product, substrate or condition in the following (a) ОН (b) Ме 1) OsO4 2) NaHSO3 (c) 1) (sia)2BH 2) NaOH/H2O2 H20arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning