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
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Organic Chemistry - Standalone book
- 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_forwardThe synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate synthesis. Draw the product of the reaction of a phenyl Gilman reagent with this epoxide. A • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Explicitly define the cis/trans stereochemistry of fused rings using wedge or hash bonds. • If enantiomers are formed, draw both. • Separate multiple products using the + sign from the drop-down menu.arrow_forward
- Compound F may be synthesised by the method below Compound A Compound F HCI CH3OH H₂SO4 Compound B CH3 CH₂ CH₂ CI NaOH Compound E K₂Cr₂O7 H₂SO4 Compound C K₂Cr₂O7 H₂SO4 Compound D a. Draw the structural formulas of compounds A, C, D, E and F in the boxes provided above. b. Draw the isomer of compound B and explain which one would be the major product and why. c. When 2-chloropropane treated with NaOH and 1-chloropropane treated with NaOH separately produce two different functional groups. Provide both reactions and explain the two different functional groups produced.arrow_forwardX Upon ozonolysis, Compound X produces two compounds: Compound Y and Compound Z. Compound Y can also be prepared from the following synthetic route: PCC 1. R₂BH, THF 1. Mg. Et₂O PCC Compound Y 2. CH₂Cl₂ 2. NaOH, HO CH₂Cl₂ 3. H₂O* From this information, draw the structures of Compounds X, Y, and Z. For Compounds X and Z, different substituents are possible. For grading purposes, just use hydrogens as the substituents. Br مرد →] ►arrow_forward1-pentanol + NaBr/H2SO4 -> 1-bromopentane Is this substitution reaction reversible? In other words, would one expect to obtain an equilibrium mixture of the alcohol and bromoalkene at the end of the reaction of would one expect this reaction to go to completion? Justify your answer?arrow_forward
- 4. A certain endothermic reaction X carried out room temperature (273K) has an enthalpy change of 20 Kcal/mol and an entropy change of 10 Kcal/K/mol. i) Calculate the Gibbs free energy (AG) of this reaction. ii) Is this reaction spontaneous or non-spontaneous? Give a reason for your answer 5. Thiomethane reacts with compound A via an SN1 reaction. Complete its reaction equation below. ii) SH Compound A ii) Draw the mechanism of reaction for this reaction. 6. Butyl Chloride undergoes an elimination reaction when reacted with sodium ethoxide to form butene. The reaction equation is given below with two reaction products A and B. low inevloa CI noitsups p *OEt B Which is the major product, and which is minor product. (Hint: Look up how the size of the base affects the elimination reaction product) Give a reason for your answer.arrow_forwardWhich of the following statements is correct?A. The haloform reaction proceeds under very difficult conditions and the yield is very low.B. The haloform reaction is used only for the identification of compounds containing secondary alcohol groups.C. Methyl ketones or alcohols are oxidized by halogens in acidic solutions to give carboxylic acids and the corresponding haloform product.D. Enolate anions react rapidly with halogens to give alpha-halocarbonyl compounds.arrow_forward1. what are the differences between acyclic and cyclic forms in terms of their physical properties? 2. what is the role of vinegar in liquid-liquid extraction?arrow_forward
- 1-pentanol + HBr -> 1-bromopentane Is this substitution reaction reversible? In other words, would one expect to obtain an equilibrium mixture of the alcohol and bromoalkene at the end of the reaction of would one expect this reaction to go to completion? Justify your answer?arrow_forwardElimination of HBr from 2-bromobutane affords a mixture of but-1-ene and but-2-ene. With sodium ethoxide as base, but-2-ene constitutes 81% of the alkene products, but with potassium tert-butoxide, but-2-ene constitutes only 67% of the alkene products. Offer an explanation for this difference.arrow_forwardb) Optical isomers can often be formed during these reactions. For products A-H indicate how many different optical isomers you expect to form for each from these reactions (you do not have to indicate whether they are diastereomers/enantiomers). c) In the preparation of substance D by ozonolysis, the second step is necessary treatment of the reaction mixture with zinc in acetic acid. If we forgot this step, we would get substance V instead of substance D, which would probably explode when isolated. What is the structure of substance V? *24 X 1: ozone V e) What products do you expect to form if they react with alkene X: I - HBr in diethyl ether; II - Brl in methanol; III - PhSCI in diethyl ether; IV - Selectfluor in methanol. P M EtOH NA EtONa PhSNa EtOH E H+ O TsCl Pyridín F- T2, Pd/C G4 mCPBA H₂SO4 10 %, H₂O 1: BH3 H◄ 2: H₂O₂ ill X Br₂ cyclohexane HCI A > В B HBr warmth, benzoylperoxid 1: ozone 2: Zn, ACOH Mg THF с D D₂O K I + J NaOHarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning