(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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Organic Chemistry (9th Edition)
- 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_forwardThe following reaction scheme contains one or more flaws. Explain what is wrong in each of the following reaction schemes and suggest how you would correct the scheme.arrow_forwardDevise 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_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).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_forwardA chemist wanted to synthesize the anesthetic 2-ethoxy-2-methylpropane. He used ethoxide ion and 2-chloro-2-methylpropane for his synthesis and ended up with no ether. What was the product of his synthesis? What reagents should he have used?arrow_forward
- Learn 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_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_forward3. Using reactions covered in this course. Suggest a synthesis scheme to produce acetaminophen (Tylenol) from phenol. 00-0 On HO acetaminophen phenol OHarrow_forward
- organolithium 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_forwardPredict the product of the hydrolysis of the following compound (1) in aqueous HCl (2) and in aqueous NaOHarrow_forwardDevise 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). Starting materials Br Reagents 1 OH a Mg/ dry ether b 1. CO₂ H3C OH 6 2. acidic workup c NaCN/THF or DMF 2 d NaCN/dil. aqueous H₂SO4 Br Br 7 3 g PBr3 OH OH e Aqueous H₂SO4 at reflux f Conc. HCI or HCI (gas) h KOH/alcohol Hot 4 8 i KMnO4 / H3O+ 5 H j Na₂ CrO4 / aqueous H₂SO4 . Å k 1. BH3/THF 2. H₂O₂/aq. NaOH Previous Nextarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning