Interpretation:
The mechanism of nucleophilic substitution of a given nucleophile to
Concept Introduction:
The nucleophilic substitution reaction occurs when alkyl halide reacts with appropriate alkoxide in the presence of alcohol to produce corresponding ether.
In a nucleophilic substitution reaction, the halide is replaced by a nucleophile.
The types of nucleophilic substitution depends on the nature of the substrate.
The
The
Carbocations intermediates occur in the
The order of reactivity of alkyl halide is tertiary > secondary> primary> methyl which undergo nucleophilic substitution
The order of reactivity of alkyl halide is tertiary < secondary<primary< methyl which undergo nucleophilic substitution
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ORGANIC CHEMISTRY VOL 2
- Starting with benzene, toluene, or phenol as the only sources of aromatic rings, show how to synthesize the following. Assume in all syntheses that mixtures of ortho-para products can be separated into the desired isomer. Q.)2,4,6-Trinitrotoluene (TNT)arrow_forwardCarbocations undergo 1,2-methyl shift or 1,2-hydride shift to produce a more stable intermediate. Give the major product(s) obtained from the reaction of the alkene with HBr.SHOW THE FORMATION OF THE CARBOCATION, THE SHIFT THAT MAY OCCUR, AND THE MAJOR PRODUCT FORMED.arrow_forwardDiphenylacetylene can be synthesized by the double dehydrohalogenation of 1,2-dibromo-1,2-diphenylethene. The sequence starting from (E)-1,2-diphenylethene consists of bromination to give the dibromide, followed by dehydrohalogenation to give a vinylic bromide, then a second dehydrohalogenation to give diphenylacetylene.(a) What is the structure, including stereochemistry, of the vinylic bromide?(b) If the sequence starts with (Z)-1,2-dibromo-1,2-diphenylethene, what is (are) the structure(s) of the intermediate dibromide(s)? What is the structure of the vinylic bromide?arrow_forward
- This problem is adapted from an experiment designed for undergraduate organic chemistry laboratories. (a) Reaction of (E)-1-(p-methoxyphenyl)propene with m-chloroperoxybenzoic acid converted the alkene to its corresponding epoxide. Give the structure, including stereochemistry, of this epoxide.(b) Assign the signals in the 1H NMR spectrum of the epoxide to the appropriate hydrogens. δ 1.4 (doublet, 3H) δ 3.8 (singlet, 3H) δ 3.0 (quartet of doublets, 1H) δ 6.9 (doublet, 2H) δ 3.5 (doublet, 1H) δ 7.2 (doublet, 2H) (c) Three signals appear in the range δ 55–60 in the 13C NMR spectrum of the epoxide. To which carbons of the epoxide do these signals correspond? (d) The epoxide is isolated only when the reaction is carried out under conditions (added Na2CO3) that ensure that the reaction mixture does not become acidic. Unless this precaution is taken, the isolated product has the molecular formula C17H17O4Cl. Suggest a reasonable structure for this product and write a reasonable mechanism…arrow_forwardThe above synthesis scheme was designed using the Organic Chemistry Roadmaps in the appendix of your textbook.In this scheme, identify the reagents necessary to accomplish the following steps in the production of (3R,4S)-3,4-dibromohexane from acetylene: Step 7 : Step 2 : Step 5arrow_forwardOn being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) produced a mixture of two alkenes B and C, each of which had the molecular formula C7H14. Catalytic hydrogenation of major isomer B or minor isomer C gave only 3-ethylpentane. Suggest structures and mechanisms for compounds A, B, and C consistent with these observations.arrow_forward
- Write four examples of the condensation reactions of carbonyl compounds, starting with benzaldehyde (C6H5CHO), with appropriate reagents and appropriate reactions. Write down the mechanism of one you want in detail.arrow_forwardWrite a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction. A. Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. B. Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. C.Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond. Cl- will act as the base in this reaction.arrow_forward1. Compound A, C9H12, absorbs 3 equivalents of H2 on catalytic hydrogenation over palladium catalyst to give B, C9H18. On the treatment with acidic KMnO4, compound A gives among other things, a ketone that was identified as cyclohexanone. On reaction with NaNH2 in NH3, followed by addition of iodomethane, compound A gives a new hydrocarbon C, C10H14. What are the structures of A , B and C?arrow_forward
- (2E,4Z,6Z,8E)-decatetraene has been cyclized to give 7,8-dimethy-1,3,5-cyclooctatriene. Predict the manner of ring-closure conrotatory or disrotatory for both thermal and photochemical reactions, and predict the stereochemistry of product in each case. Show how to get the answerarrow_forwardWhen 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be C5H10O. Propose a likely structure for this product, suggesting a reasonable mechanistic pathway for its formationarrow_forward3-chloro-1-butene reacts with sodium ethoxide in ethanol to produce 3-ethyoxy-1-butene. In the absence of sodium ethoxide, 3-chloro-1-butene reacts with ethanol to produce both 3-ethoxy-1-butene and 1-ethoxy-2-butene. Explain these results. Be sure to include mechanisms and structures in your explanation.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning