(a)
Interpretation:
The structural formulas for the products of solvolysis of given compounds are drawn.
Concept Introduction:
The
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Structure of the substrate plays a major role in
(b)
Interpretation:
Reason for the rate difference in solvolysis of given compounds should be given.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Structure of the substrate plays a major role in
(c)
Interpretation:
The stereochemistry of product that formed from the solvolysis of compound 1 has to be explained.
Concept Introduction:
The rate of the reaction is depends on a single reactant in reaction is known as
The first step of
Frist step is the slow step also rate determining step so the rate of the reaction is depends on the concentration of substrate only.
Nucleophile attacks the both front and back side of carbocation in
Order of the substrate that favored in
Structure of the substrate plays a major role in
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Chapter 9 Solutions
Organic Chemistry
- The following bicyclic ketone has two -carbons and three -hydrogens. When this molecule is treated with D2O in the presence of an acid catalyst, only two of the three -hydrogens exchange with deuterium. The -hydrogen at the bridgehead does not exchange. How do you account for the fact that two -hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of -hydrogens occurs.arrow_forwardwe know that ethers, such as diethyl ether and tetrahydrofuran, are quite resistant to the action of dilute acids and require hot concentrated HI or HBr for cleavage. However, acetals in which two ether groups are linked to the same carbon undergo hydrolysis readily, even in dilute aqueous acid. How do you account for this marked difference in chemical reactivity toward dilute aqueous acid between ethers and acetals?arrow_forwardWrite arrow-pushing mechanisms for the following reaction. Make sure that your mechanisms explain the observed stereochemistry of the transformations, if relevant.arrow_forward
- Arrange these compounds in increasing order of reactivity in SN2 nucleophilic substitution?arrow_forwardExplain the Summary of Alkyl Halides and SN1, SN2, E1, and E2 Mechanisms ?arrow_forwardStrong support for the mechanism of the nucleophilic aromatic substitutionreaction that proceeds through a benzyne intermediate comes from the reaction shown here, in which bromobenzene is treated with KNH2 in the presence of cyclopentadiene. A product that is isolated has the formula C11H10. Draw the structure of that product and explain how it validates the production of a benzyne intermediate.arrow_forward
- The carbocation electrophile in a Friedel-Crafts reaction can be generated in ways other than by reaction of an alkyl chloride with AlCl3. For example, reaction of benzene with 2-methylpropene in the presence of H3PO4 yields tert-butylbenzene. Draw a structure for the electrophile.arrow_forward1.Describe the ozonolysis of alkenes 2.one mole of a hydrocarbon(A) reacts with one mole of beomine giving a dibromo compound C5H10Br2.Substance A on treatment with cold dilute kMnO4 solution forms a compound C5C12O2(C5H12O2) on ozonolysis A,gives equimolar quantities of propanone and ethanol.Deduce the structure of substance A.arrow_forwardAn aldol condensation reaction using the reagents acetone and benzaldehyde, in the presence of sodium hydroxide was used to produce dibenzylacetone. Give a detailed NMR analysis for the product (address the issue of double bond stereochemistry; 3J values are sensitive to double bond geometry see diagram below).arrow_forward
- Consider the following statement in reference to SN1, SN2, E1, and E2 reactions of haloalkanes. To which mechanism(s), if any, does the statement apply? Involves a carbocation intermediatearrow_forwardConversion of an alkene to a halohydrin and internal displacement of a halide ion by an alkoxide ion are both stereoselective. Use this information to demonstrate that the configuration of the alkene is preserved in the epoxide. As an illustration, show that reaction of cis-2-butene by this two-step sequence gives cis-2,3- dimethyloxirane (cis-2-butene oxide).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
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning