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.

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Following is the structural formula of the principal sex pheromone of the Douglas fir tussock moth (Orgyia pseudotsugata), a severe defoliant of the fir trees of
western North America.
(Z)-6-Heneicosene-11-one
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.
• You do not have to consider stereochemistry.
• Draw the Grignard reagent as a covalent magnesium halide.
• In cases where there is more than one answer, just draw one.
P.
opy aste
Previous
Next
Transcribed Image Text:Following is the structural formula of the principal sex pheromone of the Douglas fir tussock moth (Orgyia pseudotsugata), a severe defoliant of the fir trees of western North America. (Z)-6-Heneicosene-11-one 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. • You do not have to consider stereochemistry. • Draw the Grignard reagent as a covalent magnesium halide. • In cases where there is more than one answer, just draw one. P. opy aste Previous Next
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