Pushing Electrons
4th Edition
ISBN: 9781133951889
Author: Weeks, Daniel P.
Publisher: Cengage Learning
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The formate and methoxide ions are both formed by removing a hydrogen atom from a corresponding neutral compound. Given that each process involves the breaking of an O-H bond, explain why the formate ion is so much more stable than the methoxide ion.
The substance provided can be prepared by a nucleophilic addition reaction between an aldehydeor ketone and nucleophile. Identify the reactants from which it was prepared. If the substance is an acetal, identify the carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and the amine.
What explains why many aldehydes and ketones can undergo self- condensation reactions in basic conditions?
A. The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon a an electrophile
B. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile
C. The oxygen of the carbonyl group can attack the carbon of the carbonyl group
D. Only esters can undergo self-condensation reactions
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- Account for the fact that one carboxyl group is a considerably stronger acid than the other carboxyl group.arrow_forwardAldehydes and ketones undergo condensation reaction with 2, 4-dinitrophenylhydrazine. Write an equation for the reaction of 2, 4-dinitrophenylhydrazine with any one of the pheromones. What makes 2, 4-dinitrophenylhydrazine suitable for characterizing aldehydes and ketones?arrow_forwardAldehydes undergo nucleophilic addition reactions with potent nucleophiles such as water, alcohol and amino compounds. Which of the following nucleophiles will exhibit the greatest ability to attack the electrophilic carbon in the carbonyl group of ethanal? cyclohexyl alcohol para-chlorophenol isoamyl alcohol ortho-aminophenol An aromatic ring should satisfy Huckel’s rule, wherein the number of electrons participating in the cyclic conjugation should be equal to 4n + 2. Which of the following cyclic structures does NOT obey Huckel’s rule? Cyclobutadienyl dianion Tetrahydrofuran ring Cyclopropene structure Pyrimidine ring structure What is the role of H • ions in the nucleophilic substitution of alcohols usinghydrogen halides? Removal of an alkyl groupProtonation of -OH groupStabilization of carbocationActivation of oxygen radicalarrow_forward
- Prepare the following compounds starting from benzaldehyde and the appropriate ketone. Provide reactions for preparing the ketones starting from aromatic hydrocarbon compounds.arrow_forwardExplain briefly. a. What is the major advantage of base-catalyzed hydrolysis of esters over acid-catalyzed hydrolysis? b. Why are alcoholic solutions (alcoholic NH2OHꞏHCl, alcoholic KOH, alcoholic HCl) used in the hydroxamic acid test for esters?arrow_forwardThe amines are organic weak bases which are nitrogen-containing. In the early days of organic chemistry, basic amines derived from natural sources were known as “vegetable alkali”, but they are now referred to as alkaloids. The study of alkaloids provided much of the growth of organic chemistry, phytochemistry and natural products chemistry. It remains a fascinating area of research. Please search for one naturally occurring alkaloid and provide the following: Name of the alkaloid and show its structure. Identify using arrows the polar bonds in the structure Species from where it was isolated What was the use of this alkaloid in plants (if any)? What are the pharmacological, medicinal, or environmental uses or applications of this alkaloid (if any)?arrow_forward
- Upon completion of a chemical reaction, you find you have a mixture of benzoic acid and ethyl benzoate. Propose a procedure to separate the ethyl benzoate from the mixture. You should look up the structures of benzoic acid and ethyl benzoate.arrow_forwardWhy are carbonyl compounds considered weakly acidic? Would you expect carbonyl compounds to be more acidic than alkanes? Explain.arrow_forwardOut of acid chlorides (least stable), anhydrides, esters, and amides (most stable). True or false Acid chlorides would be the most reactive to hydrolysis and Amides would be the least reactivearrow_forward
- Write the chemical equation for the acid dissociation of acetaminophen, C8H9O2N. Write the Ka expression for the acid dissociation of acetaminophen.arrow_forwardIn an esterification reaction, a carboxylic acid reacts with an excess of alcohol in acidic conditions to form an ester. Draw the structure of the ester product in the reaction between pentanoic acid and 1‑propanol. pentanoic acid+ 1-propanol= ester+ H20 structure of ester product neededarrow_forwardAldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forward
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