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-PACKAGE >CUSTOM<
- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardNH2 Br CH₂ 0= 11 COH Br Br GIVE Present a Synthesis method for Synthesizing the given product by reacting with 3-methylaniline as a Starting materialarrow_forwardH8.arrow_forward
- H3C 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_forwardSuggest a step by step mechanism for this reaction.arrow_forwardA vicinal diol has OH groups on adjacent carbons. The dehydration of a vicinal diol is accompanied by a rearrangement called the pinacol rearrangement. Propose a mechanism for this reaction.arrow_forward
- The 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_forwardFill in the reagents for the following transformations. NO2 NH2 NEN CI CNarrow_forwardH3C. H3C. CH3 nnc» XT :OH 2 CH₂OH HCI catalyst Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 H3C CH3OH H3CQ OCH3 CH3 H3C. H HO: :OCH 3 CH3 46arrow_forward
- Provide the major products of the given reaction.arrow_forwardClaisen rearrangement of an allyl phenyl ether with substituent groups in both ortho positions leads to the formation of a para-substituted product. Propose a mechanism for the following rearrangement.arrow_forwardChoose the best reagents to complete the reaction shown below. OH 00 OH OH Q Q A B C D NaOH LiF H₂O NaHarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning