Interpretation:
The name of the isomers that are separately formed under kinetically and thermodynamically control reactions of sulfonation of naphthalene is to be determined. The reason for the stability of one isomer over other is to be explained.
Concept Introduction:
On the basis of
On the basis of
Want to see the full answer?
Check out a sample textbook solutionChapter 13 Solutions
CAREY: ORGANIC CHEMISTRY
- Alcohols are important for organic synthesis, especially in situations involving alkenes. The alcohol might be the desired product, or the OH group might be transformed into another functional group via halogenation, oxidation, or perhaps conversion to a sulfonic ester derivative. Formation of an alcohol from an alkene is particularly powerful because conditions can be chosen to produce either the Markovnikov or non-Markovnikov product from an unsymmetrical alkene. Using your reaction roadmap as a guide, show how to convert 4-methyl-1-pentene into 5-methylhexanenitrile. You must use 4-methyl-1-pentene and sodium cyanide as the source of all carbon atoms in the target molecule. Show all reagents needed and all molecules synthesized along the way.arrow_forwardThe standard procedure for synthesizing a compound is the stepwise progress toward a target molecule by forming individual bonds through single reactions. Typically, the product of each reaction is isolated and purified before the next reaction in the sequence is carried out. One of the ways nature avoids this tedious practice of isolation and purification is by the use of a domino sequence in which each new product is built on a preexisting one in stepwise fashion. A great example of a laboratory domino reaction is William S. Johnsons elegant synthesis of the female hormone progesterone. Johnson first constructed the polyunsaturated monocyclic 3 alcohol (A) and then, in an acid-induced domino reaction, formed compound B, which he then converted to progesterone. A remarkable feature of this synthesis is that compound A, which has only one stereo-center, gives compound B, which has five stereocenters, each with the same configuration as those in progesterone. We will return to the chemistry of Step 2 in Section 16.7 and to the chemistry of Steps 3 and 4 in Chapter 19. In this problem, we focus on Step 1. (a) Assume that the domino reaction in Step 1 is initiated by protonation of the 3 alcohol in compound A followed by loss of H2O to give a 3 carbocation. Show how the series of reactions initiated by the formation of this cation gives compound B. (b) If you have access to a large enough set of molecular models or to a computer modeling program, build a model of progesterone and describe the conformation of each ring. There are two methyl groups and three hydrogen atoms at the set of ring junctions in progesterone. Which of these five groups occupies an equatorial position? Which occupies an axial position?arrow_forwardEarly structural studies on benzene had to explain the following experimental evidence. When benzene was treated with Br2 (plus a Lewis acid), a single substitution product of molecular formula C6H5Br was formed. When this product was treated with another equivalent of Br2, three different compounds of molecular formula C6H4Br2 were formed.a. Explain why a single Kekulé structure is consistent with the first result, but does not explain the second result.b. Then explain why a resonance description of benzene is consistent with the results of both reactions.arrow_forward
- Consider the equilibria displayed below. For which reaction is the structure on the left favored at equilibrium? a The structure on the left is favored at equilibrium for cyclohexenol/cyclohexanone only. b In both cases, the structure on the left is favored at equilibrium. c The structure on the left is favored at equilibrium for pyridin-2-ol/pyridin-2-one only. d In neither case is the structure on the left favored at equilibrium.arrow_forwardG.152.arrow_forwardorganic chemistry 6) Aniline NH₂ is best prepared byarrow_forward
- Draw the organic product that is expected to form when the following compound is oxidized under biological conditions. oxidation reduction CH₂CH₂CH₂CH.SH You do not have to consider stereochemistry. . You do not have to explicitly draw H atoms. . If no reaction occurs, draw the organic starting material. 44495 000- AIFarrow_forwardA certain hydrocarbon had the molecular formula C16H26 and contained two triple bonds. Ozonolysis gave CH3(CH2), CO₂H and HO₂CCH2CH2CH2CH2CO₂H as the only products. Draw a reasonable structure for this hydrocarbon. Click and drag to start drawing a structure. D:arrow_forwardFf.154.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning