(a)
Interpretation: The intermediates
Concept introduction: Ibuprofen is a synthetic compound which is widely used as a drug and as an analgesic and anti-inflammatory. It is synthesized from
(b)
Interpretation: The product formed by the direct alkylation of compound
Concept introduction: Ibuprofen is a synthetic compound which is widely used as a drug and as an analgesic and anti-inflammatory. It is synthesized from
Want to see the full answer?
Check out a sample textbook solutionChapter 23 Solutions
Organic Chemistry-Package(Custom)
- a) Write the structure of the Wittig reagent 2. b) Propose a step-by-step mechanism for the acid-catalyzed hydrolysis of 3 to product 4.arrow_forwardAn acid-base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers.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_forward
- Ketones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R, OH 1. HC=C: Na* 2. Hзо C. R2 R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it.arrow_forwardThe reaction of N−bromosuccinimide with 4−methyl−3−nitroanisole has been reported in the chemical literature. This reaction yields a single product in 95% yield. Identify the product formed from this starting material.arrow_forwardEsterification reactions, such as the one below, is a poor synthetic strategy as it leads to poor yields of the ester. What alternative could be done to produce more p-methylphenyl acetate? H20 HO Replace the p-methylphenol with p-chlorotoluene. Replace acetic acid with acetate. O Replace acetic acid with acetyl chloride. O Replace the aromatic alcohol with a phenolate.arrow_forward
- Please don't provide handwriting solutionarrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R OH 1. HC=C: Na* 2. H30* R2 Rí `R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • You do not have to explicitly draw H atoms. • If a group is achiral, do not use wedged or hashed bonds on it. H H3C H CH3arrow_forwardEsterification reactions, such as the one below, is a poor synthetic strategy as it leads to poor yields of the ester. What alternative could be done to produce more p-methylphenyl acetate? Replace the aromatic alcohol with a phenolate. Replace acetic acid with acetate. Replace the p-methylphenol with p-chlorotoluene. Replace acetic acid with acetyl chloride.arrow_forward
- The benzyl ether group (OBn) is often used as a protecting group for OH groups dur- ing the synthesis of complex molecules. The following structure has a number of benzyl ether groups used for this purpose. Draw the product of the following transformation. What role does the diisopropylethylamine play in this reaction? H&C H3C OBn .CI H3C H OBn OBn CH3 ОН ÓBn -OBn = 0 Diisopropylethylaminearrow_forward5 The compounds labeled benzophenone-3 (CH,O,) and benzophenone-5 (CHNAO,S) are found in certain sunscreens. Would you expect a sunscreen made with benzophenone-3 or benzophenone-5 to be more waterproof? Explain your choice.arrow_forwardH3C OH 1. Br2, PBг3 2. H₂O H3C OH Br The a-bromination of carbonyl compounds by Br₂ in acetic acid is limited to aldehydes and ketones because acids, esters, and amides don't enolize to a sufficient extent. Carboxylic acids, however, can be a-brominated by first converting the carboxylic acid to an acid bromide by treatment with PBr3. Following enolization of the acid bromide, Br2 reacts in an a-substitution reaction. Hydrolysis of the acid bromide completes the reaction. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions Br Br зь P-Br Br H₂C H₂C SH Br Brarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning