Concept explainers
Interpretation:
The synthesis for the given products is to be outlined by using benzene, toluene or aniline and any other required.
Concept introduction:
Bromination of
Grignard reagents are nucleophiles which are highly reactive, they can be obtained by reacting magnesium in diethyl ether with an alkyl or aryl bromide.
Swern oxidation of alcohols allows conversion of primary or secondary alcohols to an
Synthesis of β-hydroxyketone is possible by reacting an enolate with a carbonyl compound. Thus, various reagents can be used to convert a
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Organic Chemistry
- Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forwardCarototoxin is a natural pesticide produced by carrots, with formula C₁H2O. It undergoes hydrogenation with Pd to: give product A, C,H,O, and with Lindlar's catalyst to give product B, C,H2O. Ozonolysis followed by zinc leads to a mixture of methanal, octanal, 1,2-ethanedioic acid, 3-oxopropanoic acid, and 2-hydroxy-3-oxopropanoic acid. Draw possible structures for carototoxin, A, and B. Product B structure H2, Lindlar's Structure of carototoxin H2, Pd/C Product A structurearrow_forwardDiscovery of the antibiotic sulphanilamide led to rapid development of a large number of structurally related sulphonamides. Some of these were useful leads to compounds with other medicinal properties. Amongst these, sulfasalazine was active in the treatment of ulcerative colitis, a potentially fatal disease of the colon. As a medicinal chemist, you are about to carry out the synthesis of sulfasalazine, starting from aniline. Give the chemical names and draw the chemical structures of the reagents you will need to use for the all the steps marked (a)-(d). Aniline HO₂C HO (a) N=N- ACHN Ac represents CH3CO Sulfasalazine SO,NH S0,C1 N (b) (d) H₂N- SO,NH (c) N [Oro] SO,NH N Step (a) in question 5 above results in the para product only. Explain why this occurs.arrow_forward
- Myristoleic acid, C14H26O2, yields myristic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield pentanoic acid and nonanedioic acid. Draw the structure of Myristoleic acid.arrow_forwardUsing the necessary inorganic reagents, propose the synthesis for 2,5-diphenylfuran from benzene and succinic acid.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
- Suggest syntheses for the following compound from the indicated starting materials and any other necessary inorganic or organic compounds.arrow_forwardStearolic acid, C18H32O2, yields stearic acid on catalytic hydrogenation and undergoes oxidative cleavage with ozone to yield nonanoic acid and nonanedioic acid. What is the structure of stearolic acid?arrow_forwardSuggest the reagents for the synthesis of the following compoundsarrow_forward
- Starting with benzenc, toluene, or aniline and any other required reagents, outline a synthesis of each of the following. NH (a) CII,- (b) -CH₂CH=CCII CH, CH, CHCH₂OCH₂CH, VIR ON-O-CH-OR-O (d) O₂N- (c) H₂CH=CCH, CO₂Harrow_forwardCompound A has a formula of C7H1403. A forms yellow precipitate with NaOH/I2 but does not form silver mirror with Tollens' test. When A is subjected to acid catalyzed hydrolysis, B is formed which gives positive Tollen's test. Propose all possible structures for A C1 6arrow_forward(a) Suggest a synthesis for the following molecules starting with benzene and any other necessary reagents. (i) H2N CI (ii) OH CN 6.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning