Concept explainers
(a)
Interpretation: Products of given reactions has to be predicted.
Concept introduction: Given set of conditions gives a final product of reaction through a series of steps.
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
A strong base like
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Ester reacts with a base to form an enolate ion which attacks alkyl bromide to form an alkylated product. Hydrolysis and decarboxylation take place to form a product.
A strong base like
(b)
Interpretation: Products of given reactions has to be predicted.
Concept introduction: Given set of conditions gives a final product of reaction through a series of steps.
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Carboxylic acid undergoes
A strong base like
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Ester reacts with a base to form an enolate ion which attacks alkyl bromide to form an alkylated product. Hydrolysis and decarboxylation take place to form a product.
A strong base like
(c)
Interpretation: Products of given reactions has to be predicted.
Concept introduction: Given set of conditions gives a final product of reaction through a series of steps.
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Carboxylic acid undergoes
A strong base like
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Ester reacts with a base to form an enolate ion which attacks alkyl bromide to form an alkylated product. Hydrolysis and decarboxylation take place to form a product.
A strong base like
(d)
Interpretation: Products of given reactions has to be predicted.
Concept introduction: Given set of conditions gives a final product of reaction through a series of steps.
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Carboxylic acid undergoes
A strong base like
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Ester reacts with a base to form an enolate ion which attacks alkyl bromide to form an alkylated product. Hydrolysis and decarboxylation take place to form a product.
A strong base like
(e)
Interpretation: Products of given reactions has to be predicted.
Concept introduction: Given set of conditions gives a final product of reaction through a series of steps.
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Carboxylic acid undergoes
A strong base like
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Ester reacts with a base to form an enolate ion which attacks alkyl bromide to form an alkylated product. Hydrolysis and decarboxylation take place to form a product.
A strong base like
(f)
Interpretation: Products of given reactions has to be predicted.
Concept introduction: Given set of conditions gives a final product of reaction through a series of steps.
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Carboxylic acid undergoes
A strong base like
Ester reacts with a base to form an enolate ion which undergoes intramolecular reaction.
Ester reacts with a base to form an enolate ion which attacks alkyl bromide to form an alkylated product. Hydrolysis and decarboxylation take place to form a product.
A strong base like
Want to see the full answer?
Check out a sample textbook solutionChapter 17 Solutions
EBK ORGANIC CHEMISTRY
- 1. Write the structure of the major organic product formed when nonanoyl chloride is each of the following reagents: A. Aqueous acid (H3O*) B. Ethanol in the presence of triethylamine C. Excess diethylamine (at least 2 equivalents) D. Sodium acetate E. Lithium aluminum hydride in diethyl ether F. (CH3CH2)2CuLi Cou onch of the following reactionsarrow_forwardDraw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwolfia serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.arrow_forward6. Write reactions for: A) benzaldehyde + NaOH / H₂O B) acetophenone + KCN / HCN C) butyraldehyde + NaSH / H₂S D) acetaldehyde + CH3ONA / CH3OH E) phenylacetaldehyde + HOCH₂CH₂OH / OH s'diners eritarrow_forward
- Draw a stepwise mechanism for the following reactions, two steps in R. B. Woodward’s classic synthesis of reserpine in 1958. Reserpine, which is isolated from the extracts of the Indian snakeroot Rauwola serpentina Benth, was used at one time to manage mild hypertension associated with anxiety.arrow_forwardWhat compound is the limiting reagent?arrow_forwardIdentify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. 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 (1 H) ppm. What is the structure of B?arrow_forward
- Identify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.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 (1 H) ppm. What is the structure of B?arrow_forward1. Br₂, PBrg 2. H₂O H₂C OH 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 α- 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 H3C :0: :0::Br: Br Br H3C CO-P H Br Brarrow_forwardH3C. 00 H3C. CH3 XII HO: OCH3 Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions 2 CH₂OH HCI catalyst CH3 H3C H-OH₂ H3CO OCH3 CH3 H3C. H₂O: OCH3 CH3 H₂O Чаarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning