Concept explainers
Interpretation:
From the given data, the structure of the product of the given reaction is to be identified.
Concept introduction:
The
Thus, both can react with the nucleophile, depending on the nature of the nucleophile and the regioselectivity of the reaction.
When the nucleophile adds to the carbonyl carbon, the reaction yields a
When the nucleophile adds to the
The number of signals in the
A broad absorption between
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Organic Chemistry: Principles and Mechanisms (Second Edition)
- Provide a synthesis for the following transformation OHarrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardIdentify products A and B from the given 1H NMR data. Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1H) ppm. What is the structure of B?arrow_forward
- What carbonyl compound and what phosphonium ylide are needed to synthesize the following compounds?arrow_forwardIdentify the reagents represented by the letters a-e in the following scheme:arrow_forwardMinoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction.arrow_forward
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardTamoxifen is a drug used in the treatment of breast cancer. How would you prepare tamoxifen from benzene, the following ketone, and any other reagents needed?arrow_forward
- Following is the structure of miconazole, the active antifungal agent in a number of over-the-counter preparations, including Monistat, that are used to treat vaginal yeast infections. One of the compounds needed for the synthesis of miconazole is the trichloro derivative of toluene shown on its right. (a) Show how this derivative can be synthesized from toluene. (b) How many stereoisomers are possible for miconazole?arrow_forwardGive the major products or reagents represented by letters E and F:arrow_forwardPredict the product based on the following data: H-NMR: 0.93 ppm (3H, triplet); 1.57 ppm (2H, multiplet – looks like “pentet”); 2.14 ppm (3H,singlet), 2.26ppm (2H, triplet); 3.42 ppm (1H, triplet); 4.83 ppm (1H, multiplet) Weight of product: 156 g/mol IR: Two sharp peaks at 1784 cm-1 and 1742 cm-1 C-NMR: 9.9 ppm; 29.0 ppm; 29.8 ppm; 31.8 ppm; 52.9 ppm; 76.1 ppm; 181.1 ppm; 200.2 ppmarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning