Concept explainers
Interpretation: The correct sterochemical descriptor for the substitution pattern of the cyclopropane ring in permethrin and bifentrin has to be determined.
Concept introduction:
Cis compounds are the geometrical isomers with the organic groups on the same side of the double bond.
The double bond of
In a cis isomer, groups are attached on the same side of the double bond while in the Trans isomer the groups are attached on the opposite sides.
Simple representation of cis and Trans isomer is as follows,
Permethrin and bifenthrin are the synthetic pyretherenoids now in common use in household and agricultural products.
Their structures are given below,
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Chapter 17 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
- Digitalis is a preparation made from the dried seeds and leaves of the purple foxglove, Digitalis purpurea, a plant native to southern and central Europe and cultivated in the United States. The preparation is a mixture of several active components, including digitalin. Digitalis is used in medicine to increase the force of myocardial contraction and as a conduction depressant to decrease heart rate (the heart pumps more forcefully but less often).arrow_forwardLipoic acid is required by many microorganisms for proper growth. As a disulfide, it functions in the living system by catalyzing certain oxidation reactions and is reduced in the process. Write the structure of the reduction product.arrow_forwardPermethrin and Bifenthrin Pyrethrin is a natural insecticide obtained from the powdered flower heads of several species of Chrysanthemum. The active substances in pyrethrum, principally pyrethrins I and II, are contact poisons for insects and cold-blooded vertebrates. Although powders made from Chrysanthemum extracts have found widespread use, the active substances in them are destroyed rapidly in the environment. In an effort to develop synthetic compounds as effective as the natural insecticides but with greater biostability, chemists prepared a series of esters related in structure. Among the synthetic pyrethrenoids now in common use in household and agricultural products are permethrin and bifenthrin. As discussed above, the natural products pyrethrins I and II (not shown) are destroyed rapidly in the environment. One of the key changes in the structures of permethrin and bifenthrin relative to the pyrethrins was the substitution of naturally occurring methyl groups on the alkene with electron withdrawing groups (EWGs) such as chlorine and trifluoromethyl. What reactions of the alkene would the change of methyl groups to EWGs retard? 1. Oxidation of the double bond. 2. Electrophilic addition reactions. 3. Nucleophilic addition reactions. 4. Both 1 and 2. 5. All of the above.arrow_forward
- Vanilla flavoring is either extracted from a tropical orchid or synthetically produced from wood pulp by-products. What differences in chemical structure would you expect in these two commercial products: vanilla extract and imitation vanilla extract?arrow_forwardAccount for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forwardExplain the solubility behavior of each compound in water with relevance to their STRUCTURE. b. Amines in water-Aniline (two layers; clear colorless layer at the bottom and yellowish layer at the top)-N,N-dimethylaniline (two layers; clear colorless layer at the bottom and yellowish layer at the top)-Diethylamine (clear colorless solution)arrow_forward
- What reactions and reagents can be used to make phenol from benzene if electrophilic aromatic substitution reactions are excluded and benzene is the only source of carbon?arrow_forwardGiven a chemical test to distinguish between:(i) Ethane and ethane(ii) Ethanol and ethanoic acid(iii) Soaps and Detergentsarrow_forwardDibenzalpropanone is a compound that can absorb UV rays and can be used as a sunscreen. Write down the reagents used to synthesize the compound dibenzalpropanone.arrow_forward
- Ciprofloxacin is a member of the fluoroquinolone class of antibiotics.(a) Which of its rings are aromatic?arrow_forwardGive the chemical tests to distinguish between following pair of compounds : (i) Propanol and propanone (ii) Ethyl acetate and methyl acetate (iii) Benzaldehyde and benzoic acid (iv) Benzaldehyde and acetaldehyde (v) Formic acid and acetic acid (vi) Propanal and propanol (vii) Ethanoic acid and ethylethanoatearrow_forwardConsider the following compounds: Compound E: benzoic acid Compound F: benzoyl chloride Compound G: benzamide Compound H: benzaldehyde a) Identify the compound can be oxidised into compound E. b) Select one compound that can undergo alcoholysis to yield an ester. c) Select two compounds which áre known as carboxylic acid derivatives.arrow_forward
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