Pyrethrins are a group of naturally occurring insecticidal substances found in the flowers of various plants of the chrysanthemum family. The following is the structure of a typical pyrethrin, cinerin I (exclusive of stereochemistry):
(a) Locate any isoprene units present in cinerin I.
(b) Hydrolysis of cinerin I gives an optically active carboxylic acid,
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ORGANIC CHEMISTRY W/CONNECT
- An unknown hydrocarbon A with the formula C6H12 reacts with 1 molar equivalent ofH2 over a palladium catalyst. Hydrocarbon A also reacts with OsO4 to give diol B. When oxidized with KMnO4 in acidic solution, A gives two fragments. One fragmentis propanoic acid, CH3CH2CO2H, and the other fragment is ketone C. What are thestructures of A, B, and C? Write all reactions and show your reasoning.arrow_forwardOn being heated with a solution of sodium ethoxide in ethanol, compound A (C7H15Br) yielded a mixture of two alkenes B and C, each having the molecular formula C7H14. Catalytic hydrogenation of the major isomer B or the minor isomer C gave only 3-ethylpentane. Suggest structures for compounds A, B, and C consistent with these observations.arrow_forwardAn organic compound A of unknown structure was found to have a molecular formula C8H16. When A was poured in water and heated, compound B having a molecular formula C8H18O was formed. B upon heating with sulfuric acid was converted to C as the major product which is identical to A. Ozonolysis of C gave one molecule each of two different products D and E, both having a molecular formula C4H8O. Write the reactions involved and determine the structure of A,B,C,D and E.arrow_forward
- A compound A, C7H12, was found to be optically active. On catalytic reduction over platinum catalyst, 2 equivalents of hydrogen were absorbed, yielding compound B, C7H16. On ozonolysis of A, two fragments were obtained. One fragment was identified as acetic acid. The other fragment, compound C, was an optically active carboxylic acid, C5H10O2. Write the reactions and draw structures for A, B and C.arrow_forwardTwo moles of organic compound ‘A’ on treatment with a strong base gives two compounds ‘B’ and ‘C’. Compound ‘B’ on dehydrogenation with Cu gives ‘A’ while acidification of ‘C’ yields carboxylic acid ‘D’ with molecular formula of CH2O2. Identify the compounds A, B, C and D and write all chemical reactions involved.arrow_forwardChemical compound A is an alkene that when treated with ozone followed by treatment of Zn in HOAc produces only (CH3CH2CH2) 2C = O. What is the structure of A? If A is reacted with peroxyacetic acid, what product would be obtained? Write the corresponding structure. Is this substance optically active? Please include a detailed explanation.arrow_forward
- Compound AA has a molecular formula of C3H6O and gives a positiveresult using Tollen’s reagent. The reaction of compound AA with hotacidified potassium permanganate, KMnO4 gives compound BB. Thecatalytic hydrogenation of compound AA with nickel, Ni producedcompound CC. The reaction of compound BB with ethanamine,CH3CH2NH2 produces compound DD I) Draw the structural formula of compounds AA, BB, CC and DD. 2)Name the type of chemical reaction for the formation of compound CC.arrow_forwardThe sex attractant of the housefly has the formula C23H46. When treated with warm potassium permanganate, this pheromone gives two products: CH3(CH2)12COOH and CH3(CH2)7COOH. Suggest a structure for this sex attractant. Explainwhich part of the structure is uncertainarrow_forwardThe compound acetophenone has a very similar molar mass to that of benzoic acid and benzamide. However, acetophenone has a much lower m.p. (20 °C) than both such that, by contrast, it is a liquid at room temperature. By considering intermolecular forces and comparing functional group structure, account for this big difference in physical properties.arrow_forward
- Compound A, C11H16O, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H2SO4, dehydration occurred and an optically inactive alkene B, C11H14 was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C8H8O, was shown to be a methyl ketone while product D, C3H6O, was shown to be an aldehyde.arrow_forwardDraw the structure of sodium tetradecyl sulfate and ciprofloxacin and state how the activity of the drug is influenced by alkane groupings.arrow_forwardQuinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring, are commonly synthesized by a method known as the Skraupsynthesis, in which aniline reacts with glycerol under acidic conditions. Nitrobenzene is added to the reaction mixture to serve as an oxidizing agent.The first step in the synthesis is the dehydration of glycerol to propenal. a. What product would be obtained if para-ethylaniline were used instead of aniline?b. What product would be obtained if 3-hexen-2-one were used instead of glycerol?c. What starting materials are needed for the synthesis of 2,7-diethyl-3-methylquinoline?arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning