Concept explainers
Interpretation:
The reagents involved in given reactions are to be determined.
Concept introduction:
Primary alcohols on oxidation with PCC form aldehyde while secondary alcohols require drastic conditions like chromic acid to form
Treatment of
Carbonyl compounds react with alcohol to form acetals. First, one molecule of alcohol reacts with carbonyl to form hemiacetal followed by another alcohol molecule to form acetals.
Acetals and hemiacetals can be cleaved through acidic hydrolysis to form carbonyl compound and alcohol.
Carbonyl compounds react with Grignard reagent followed by hydrolysis to form alcohols.
On the reaction of an alkene with ozone, carbonyl compounds are formed.
Carbonyl compounds undergo Wolff–Kishner reduction on reaction with hydrazine and then potassium hydroxide to form
Ketones react with peracids to form esters by migration of one of the alkyl or aryl group.
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ORGANIC CHEM. VOL.1+2-W/WILEYPLUS
- Propose an efficient synthesis of (C) and (D) of the following transformationsarrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forwardIdentify the major product in each of the following reactions:arrow_forward
- Draw the products obtained in each of the following reactions: (c) (a) H₂C H3C CH3 CH 3 CH3 CH 3 HCI CH3OH HCI CH3OH (d) (b) H₂C H3C CH3 CH₂0 CH3OH CH3 CH₂ CH3 CH₂00 CH3OHarrow_forwardIdentify the major product in each of the following reactions:arrow_forward11.21 Propose an efficient synthesis for each of the following transformations: (a) (b) (c) OH - d) H e) Harrow_forward
- Rank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forwardRank the compounds in each group according to their reactivity toward electrophilic substitution: (a) Chlorobenzene, o-dichlorobenzene, benzene (b) p-Bromonitrobenzene, nitrobenzene, phenol (c) Fluorobenzene, benzaldehyde, o-dimethylbenzenearrow_forward4.33 Select the compound in each of the following pairs that will be converted to the corresponding alkyl bromide more rapidly on being treated with hydrogen bromide. Explain the reason for your choice. (a) 1-Butanol or 2-Butanol (b) 2-Methyl-1-butanol or 2-butanol (c) 2-Methyl-2-butanol or 2-butanol (d) 2-Methylbutane or 2-butanol (e) 1-Methylcyclopentanol or cyclohexanol Draw the energy diagrams of an SN1 reaction and an SN2 reaction. Include in your drawing anexample reaction. Identify the rate limiting step and label it as unimolecular or bimolecular.arrow_forward
- Compound A (C9H18O) forms a phenylhydrazone, but it gives a negative Tollens’ test. The IR spectrum of A has a strong band near 1710 cm−1 . The broadband carbon NMR spectrum of A is given below. a)Propose a structure for A and explain how your structure fits the spectral data. b) Propose a mechanism for this reaction.arrow_forwardThe following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxidearrow_forwardREACTIONS Indicate the reagent(s) needed to carry out the following transformations. a) он COTS b) онarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning