Concept explainers
When m-chlorotoluene is treated with sodium amide in liquid ammonia, the products of the reaction are
Want to see the full answer?
Check out a sample textbook solutionChapter 15 Solutions
ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
Additional Science Textbook Solutions
Chemistry: The Molecular Nature of Matter
General Chemistry: Principles and Modern Applications (11th Edition)
Chemistry (7th Edition)
General, Organic, and Biological Chemistry (3rd Edition)
Principles of Chemistry: A Molecular Approach (3rd Edition)
- Aldehydes and ketones react with thiols to yield thioacetals just as they react with alcohols to yield acetals. Predict the product of the following reaction, and propose a mechanism:arrow_forwardA step in a synthesis of PGE1 (prostaglandin E1, alprostadil) is the reaction of a trisubstituted cyclohexene with bromine to form a bromolactone. Propose a mechanism for formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. Alprostadil is used as a temporary therapy for infants born with congenital heart defects that restrict pulmonary blood flow. It brings about dilation of the ductus arteriosus, which in turn increases blood flow in the lungs and blood oxygenation.arrow_forwardAcid-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_forward
- Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1H-NMR spectrum, deduce the structure of compound I.arrow_forwardNonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardAmines are converted into alkenes by a two-step process called Hofmann elimination. SN2 reaction of the amine with an excess of CH3I in the first step yields an intermediate that undergoes E2 reaction when treated with silver oxide as base. Pentylamine, for example, yields 1-pentene. Propose a structure for the intermediate, and explain why it readily undergoes elimination.arrow_forward
- Enamines normally react with methyl iodide to give two products: one arising from alkylation at nitrogen and the second arising from alkylation at carbon. For example, Heating the mixture of C-alkylation and N-alkylation products gives only the product from C-alkylation. Propose a mechanism for this isomerization.arrow_forwardPropose syntheses of the following compounds from benzene: (a) N, N-Dimethylaniline (b) p-Chloroaniline (c) m-Chloroaniline (d) 2, 4-Dimethylanilinearrow_forwardWhen 2,2-dibromo-1-phenylpropane is heated overnight with sodium amide at 150 °C, the major product (after addition of water) is a different foul-smelling compound of formula C9H8. Propose a structure for this product, and give a mechanism to account for its formation.arrow_forward
- 8arrow_forwardD H,O* CH,CI H,SO, H3C KMNO, + + ΗΝO, H A AICI, AICI, A Cl, FeCl, F+ G 7. Based on the reaction scheme above: (a) Draw the structural formula for compound A to H. (b) Show the mechanism for the formation of compound C. (c) Explain why the activating group, such as -OH is ortho and para director. Give an example of a compound from the reaction scheme. (d) Explain why a deactivating group, such as -NO2 is a meta director. Give an example of compound from the reaction scheme. Br2 FeBr3arrow_forwardCompound A produce compound D while undergo Friedel Crafts Alkylation. Compound D is then oxidized and produce compound E (C11H12O3) as a major product.What are the possible structural formula of compound D and E?arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning