(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
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Organic Chemistry
- What reagents would you use to convert methyl propanoate to the following compounds? a. isopropyl propanoate b. sodium propanoate c. N-ethylpropanamide d. propanoic acidarrow_forwardIn each reaction box, place the best reagent and conditions from the available reagent list. 1. MCPBA 2. OH 3. 4. Answer Bank В,Н, Н, О, SOCI, H;O* O3 HBr I,, NaOH THF H,CO CH;MgBr Br, KMNO4 CH,SCH,arrow_forward3. Imitation vanilla extract contains vanillin and propylene glycol. Analysis via GC-MS shows a small quantity of a racemic mixture of a vanillin-propylene glycol acetal. Draw the structure of this acetal (considering stereochemistry) and briefly explain why it is racemic. HO H3CO vanillin H HO OH propylene glycolarrow_forward
- Which one-carbon group is carried by N5-methyl-tetrahydrofolate? A. Carbon dioxide B. aldehyde C. methyl D. hydroxymethylarrow_forwardWhat is the purpose of the first step of this reaction? OH 1. CH;CH,OH, H* 2. LIAIH4, Et,0 3. H*, H,0 Create an enolate on the a-carbon Reduce the ester Protect that aldehyde as an acetal Hydrolyze the ester to promote reactivity of the carboxylic acid derivativearrow_forward3. Consider the following equilibrium for questions 3a, 3b, and 3c. OMe OMe НО H. H. pka = 7.4 pKa = 10 3a. What side of the equilibrium is favored? 3b. Using curved arrows, give a mechanism for this reaction from left to right. 3c. What is the role of triethyl amine in the synthesis of divanillyl oxalate? That is, how does the addition of triethyl amine impact the nucleophilicity of vanillin?arrow_forward
- p-toluic acid is prepared from 3.42 grams of p-Bromotoluene. When p-Bromotoluene was mixed with dry ether, the mixture was warmed until the ether begins to boil (34.6 °C). When the reaction is almost complete, dry ice (3-4 mL in a beaker) was prepared and the mixture was poured into it. After some time, 5 mL of 6 N HCl was added. The solvent used for the recrystallization is 100 mL of 30% ethanol. The reaction equation is given on the figure. What is the actual yield? What is the theoretical yield? How many moles of p-toluic acid was produced?arrow_forwardExplain the relevance pi* (antibonding) -molecular orbitals have in nucleophilic addition reactions of carbonyl containing compounds.arrow_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. 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_forward
- Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system. a. How can tyramine be prepared from β-phenylethylamine?b. How can dopamine be prepared from tyramine?c. Give two ways to prepare β-phenylethylamine from β-phenylethyl chloride.d. How can β-phenylethylamine be prepared from benzyl chloride?e. How can β-phenylethylamine be prepared from benzaldehyde?arrow_forwardWrite the equation for the following reactions. Name and write the structure of the major product formed in the given reaction. a. isopentylbromide + NH3(aq) b. N,N-dimethylaniline + acetic acid c. ethyl-n-butylamine + benzyl chloride d. ethylpropylamine + benzoyl chloride e. isopentylamine + acetoyl chloridearrow_forwarda-phellandrene and ß-phellandrene are two isomeric diene-containing terpene compounds isolated from eucalyptus plants that are used in fragrances due to their minty and citrusy odors. Use these two compounds to answer the following two questions: a. The addition of 1 equivalent of bromine at room temperature to the phellandrenes will give three possible di-brominated products. Select either a- or ß-phellandrene for this question and draw it in the left box - you can answer this question with either isomer. Draw all three products in the colored boxes depicted - you do not need to depict newly formed stereocenters or show mechanisms. OR a-phellandrene B-phellandrene product 1 select either a- or B-phellandrene product 2 Br₂ room temperature 3 possible products (see below) product 3arrow_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