(a)
To determine: The product from the given reaction.
Interpretation: The given question stated that Professor Patrick Dussault has developed an alternative to the standard two step ozonolysis procedure requires reduction of the ozonide in a second step. Pyridine is used as a basic organic solvent in a one step process. The desired product from the given reaction is to be predicted.
Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where
(b)
To determine: The major product of the given reaction.
Interpretation: The major product of the given reaction is to be predicted
Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where
(c)
To determine: The major product of the given reaction.
Interpretation: The major product of the given reaction is to be predicted.
Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where
(d)
To determine: The major product of the given reaction.
Interpretation: The major product of the given reaction is to be predicted.
Concept introduction: Ozonolysis is the oxidative cleavage of the double bond, where
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EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- Predict the major organic product of the following reaction sequence. Styrene (1.53 g, 0.011 mol) in methanol (30 mL) was added to a mixture of Hg(OAc)2 (5.30 g, 0.016 mol) in methanol (100 mL) at room temp. and stirred for 24 h. Sodium hydroxide (3.0 M, 16 mL) was added, followed by NaBH4 (0.32 g, 0.008 mol) in NaOH (3.0 M, 16 mL) at 0 °C. The precipitated Hg was removed by filtration. The product was isolated by diethyl ether extraction. After drying over NazSO4, solvent was removed and distillation gave the product. (Adapted from: Senda, Y.; Kanto, H.; Itoh, H. J. Chem. Soc., Perkin Trans. 2 1997, 1143-1146.)arrow_forwardBecause phenol (C6H5OH) is less acidic than a carboxylic acid, it can be deprotonated by NaOH but not by the weaker base NaHCO3. Using this information, write out an extraction sequence that can be used to separate C6H5OH, benzoic acid, and cyclohexanol. Show what compound is present in each layer at each stage of the process, and if it is present in its neutral or ionic form.arrow_forwardthis drug contains one or more building blocks derived from either ethylene oxide or epichlorohydrin.Identify the part of each molecule that can be derived from one or the other of the building block and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule.arrow_forward
- Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the starting material followed by the letters of the reagents you would use beginning with the first step. The answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h). HO, Starting materials Br Br ton HO. OH H. H3C 1 2 3 он он Br 7 Reagents a Mg / dry ether e Ethanol, H2SO4(trace) at reflux i Os04 b 1. CO2 2. acidic workup f Conc. HCI į Naz Cro4 / aqueous H,SO4 c NACN / THF or DMF 9 HBr k 1. BH3/THF 2. H2O2/aq. NAOH d NaCN / dil. aqueous H2SO4 h КОН/alcoholarrow_forwardGive an explanation, why the acidity of these phenolic derivatives give these pKa value? Describe it by using the electronic effect on the acidity.arrow_forwardPredict the products of the reaction of the below reagents with either acetophenone or phenylacetaldehyde. NaBH4, H3O+ HCN, KCN H2NNH2 CH3MgBr, then H3O+ NH2OH, catalytic acidarrow_forward
- In the reaction of the phenol nitration, a mixture of o-nitrophenol and p-nitrophenol is formed. The melting point of nitrophenol is 45, the melting point of p-nitrophenol is 112 ° C. How would you interpret this difference depending on their molecular structure?arrow_forwardorganolithium reagents are strong bases. Because of this, they cannot be prepared from compounds that contain acidic groups (-OH, -NH:, -NHR, -SH, -C=CH, RCO:H) or compounds that have carbonyl groups. Which of the given syntheses of a Grignard reagent below would fail to form as written? Circle the answer and explain your choice Br Mg, ether MgBr 1) Mg, ether Mgl 2) Br Mg. ether MgBr 3) но но 2. Predict the major products for the following reactions with the correct stereochemistry were necessary. SOCI, LOH OH OH SOCI NBS ight NBS G light Me (CH, Cel Br MgBrarrow_forward8. Using only ethylacetate, acetone, benzaldehyde, or benzyl bromide as organic components, and using any bases you desire, indicate a method to synthesize the following compounds: 요요 ilarrow_forward
- Dd.84.arrow_forwardA lithium diorganocopper (Gilman) reagentarrow_forwardLearn the term “oxime” and then look up a reaction called the “Beckmann rearrangement.” Why is this reaction useful for the synthesis of acetaminophen? Propose the structure of an oxime that would yield acetaminophen if subjected to the Beckmann rearrangement.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning