Concept explainers
Interpretation:
The structure of products of the given reactions is to be determined.
Concept introduction:
The compound
The compound
Diels-Alder reaction is a reaction that takes place between two organic compounds, such that one is a conjugated diene and the other is a substituted
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EBK ORGANIC CHEMISTRY
- -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the molecular formula C10H16 and a UV absorption maximum at 232 nm. On hydrogenation with a palladium catalyst, 2,6-dimethyloctane is obtained. Ozonolysis of -ocimene, followed by treatment with zinc and acetic acid, produces the following four fragments: (a) How many double bonds does -ocimene have? (b) Is -ocimene conjugated or nonconjugated? (c) Propose a structure for -ocimene. (d) Write the reactions, showing starting material and products.arrow_forwardAlpha-phellandrene, C₁0H₁6, is a pleasant-smelling chiral compound that may be obtained from the leaves of eucalyptus trees. It has the molecular formula C₁0H16 and a UV absorption maximum at 263 nm. On hydrogenation with a palladium catalyst, an achiral hydrocarbon with the formula C₁0H20 is obtained. Ozonolysis of alpha-phellandrene, followed by treatment with zinc and acetic acid, produces the following two compounds: 0 || CH3C-CH 0 || ● Propose a structure for alpha-phellandrene. (+ || HCCH₂CHCH I CH(CH3)2 • You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. n [ ]# ?arrow_forward(a) The Friedel-Crafts reaction of benzene with 2-chloro-3-methylbutane in the presence of AlCl3 occurs with a carbocation rearrangement. Give mechanistic explanation and the product formed. (b) Predict the product(s) will be formed from the following reactions: (i) Bromination of p-methylbenzoic acid (ii) Sulphonation of m-bromoanisole (iii) Friedel-craft acylation of o-bromonitrobenzenearrow_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_forwardCompound A whose molecular formula is C9H11ClO, is found to be aromatic, and on vigorous oxidation with hot, concentrated, basic potassium permanganate followed by acidification, a new aromatic, compound B with the molecular formula of C7H5ClO2 is formed. On treatment with bromine and a ferric bromide catalyst, compound B produces ONLY 2 monobrominated derivatives, compounds C and D, each having the molecular formula C7H4BrClO2. On treatment with sodium metal, compound A produces bubbles of hydrogen gas. Controlled oxidation of compound A with PCC first gives compound E, with formula C9H9ClO. Compound E produces a silver mirror with Tollen’s reagent. Mild oxidation of compound E by chromic acid produces compound F, with the molecular formula C9H9ClO2 which turns blue litmus red. When compound A is heated with concentrated sulfuric acid, a single compound G, whose molecular formula is C9H9Cl, is produced. On ozonolysis followed by reaction with dimethyl sulfide, compound G gives…arrow_forwardKk.242.arrow_forward
- In an aqueous solution containing sodium bicarbonate, aniline reacts quickly withbromine to give 2,4,6-tribromoaniline. Nitration of aniline requires very strong conditions,however, and the yields (mostly m-nitroaniline) are poor.(a) What conditions are used for nitration, and what form of aniline is present under theseconditions?arrow_forwardCompound A was oxidized with periodic acid to give B, which after acid hydrolysis gave C. Bromine oxidation of C gave D. Suggest structural formulas, including stereochemistry, for compounds B, C, and D.arrow_forwardPractice Problem 19.54 Z Your answer is partially correct. Try again. Predict the major product(s) (A - K) from the treatment of acetone with the following compounds (a-c): NH2 HO Eto OEt A: B: C: D: E: F: OH OH но CN G: H: I: J: (a) [H*], excess EtOH, (-H20) Major Product(s): (ь) NaBH4, Meон B Major Product(s): (c) LAH followed by H20 Major Product(s): SHOW HINTarrow_forward
- Rank 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_forwardWolff-Kishner reduction of compound W gave compound A. Treatment of A with m-chloroperbenzoic acid gave B which on reduction with LiAH4 gave C. Oxidation of compound C with chromic acid gave D (C9H14O). Suggest the structures for A, B, C, and D.arrow_forwardStarting exactly with any acid chloride with exactly with 5 carbon atoms, and using appropriate reagents outline the synthesis of the following molecules: (a) 2,6-dimethyl-4-heptanone (b) 4-propyl-4-octanolarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning