Several syntheses of this compound have been reported, one of which is shown: Br ketone alkyl bromide (Z)-6-Heneicosene-11-one This synthesis involves the following steps: 1. The ketone is protected by the reaction with 1,2-ethanediol to form acetal 1; 2. Acetal 1 is deprotonated with NaNH2 to form acetylide anion 2; 3. Acetylide anion 2 reacts in an SN2 reaction with the alkyl bromide to form alkyne 3; 4. Alkyne 3 is hydrolyzed to form ketone 4; 5. Ketone 4 reacts with H2 and Lindlar's catalyst to form (Z)-6-Heneicosene-11-one. Diagram these steps on a separate sheet of paper, and then draw the structure of ketone 4.

Several syntheses of this compound have been reported, one of which is shown: Br ketone alkyl bromide (Z)-6-Heneicosene-11-one This synthesis involves the following steps: 1. The ketone is protected by the reaction with 1,2-ethanediol to form acetal 1; 2. Acetal 1 is deprotonated with NaNH2 to form acetylide anion 2; 3. Acetylide anion 2 reacts in an SN2 reaction with the alkyl bromide to form alkyne 3; 4. Alkyne 3 is hydrolyzed to form ketone 4; 5. Ketone 4 reacts with H2 and Lindlar's catalyst to form (Z)-6-Heneicosene-11-one. Diagram these steps on a separate sheet of paper, and then draw the structure of ketone 4.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 50AP: -Ocimene is a pleasant-smelling hydrocarbon found in the leaves of certain herbs. It has the...

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