Concept explainers
The sex attractant of the female winter moth has been identified as the tetraene
hexadecadien
ol and allyl alcohol.
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Chapter 18 Solutions
Organic Chemistry - Standalone book
- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardProvide reagents and conditions to produce the products indicated. EN OH H3C CH3 HO HOarrow_forwardProvide synthetic routes for the preparation of the starting materials of azo dye Alizarine Yellow R starting from benzene O₂N -NEN OH CO₂Harrow_forward
- Treating cyclohexene with HBr in the presence of acetic acid gives bromocyclohexane (85%) and cyclohexyl acetate (15%). Br OCCH CH,COH + HBr Bromocyclohexane Cyclohexyl acetate (15%) Cyclohexene (85%) Propose a mechanism for the formation of the latter product.arrow_forwardWhen 1,2-epoxycyclohexane (cyclohexene oxide) is treated with anhydrous HCl inmethanol, the principal product is trans-2-methoxycyclohexanol. Propose a mechanismto account for the formation of this product.arrow_forwardTreatment of 3-chloro-2-cyclohexenone with sodium ethoxide in methanol gives 3-ethoxy-2-cyclohexene. Propose a mechanism for this reaction that accounts for the formation of the product.arrow_forward
- Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.arrow_forwardH3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3arrow_forwardThe sex attractant of the female winter moth has been identified as the tetraene CH3(CH2)8CH=CHCH2CH=CHCH2CH=CHCH=CH2. Devise a synthesis of this material from 3,6-hexadecadien-1-ol and allyl alcohol.arrow_forward
- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis. H+ +H HO НО COH + HO 1,4-Dioxanearrow_forwardChoose reagents to convert 2-cyclohexenone to the following compounds.arrow_forwardFill in the reagents for the following transformations. NO2 NH2 NEN CI CNarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning