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. Several syntheses of this compound have been reported, one of which is shown: O. _OH Br (Z)-6-Heneicosene-11-one alkyl bromide 1 hemiacetal 1 alkyl bromide 2 Br This synthesis involves the following steps: 1. Alkyl bromide 2 reacts with triphenylphosphine and butyllithium to form ylide 1; 2. Hemiacetal 1 is in equilibrium with aldehyde 2; 3. Aldehyde 2 reacts with ylide 1 to form oxaphosphetane 3; 4. Oxaphosphetane 3 expels triphenylphosphine oxide to form alkene 4 (the alkene is primarily formed in the desired Z configuration); 5. Alkene 4 is oxidized with PCC to form aldehyde 5; 6. Alkyl bromide 1 reacts with magnesium and ether to form Grignard reagent 6; 7. Grignard reagent 6 adds to aldehyde 5 to form tetrahedral intermediate 7; 8. Tetrahedral intermediate 7 reacts with dilute aqueous acid to form alcohol 8; 9. Alcohol 8 is oxidized with chromic acid to yield (Z)-6-Heneicosene-11-one. Diagram these steps on a separate sheet of paper, and then draw the structure of oxaphosphetane 3. • 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. (Z)-6-Heneicosene-11-one
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. Several syntheses of this compound have been reported, one of which is shown: O. _OH Br (Z)-6-Heneicosene-11-one alkyl bromide 1 hemiacetal 1 alkyl bromide 2 Br This synthesis involves the following steps: 1. Alkyl bromide 2 reacts with triphenylphosphine and butyllithium to form ylide 1; 2. Hemiacetal 1 is in equilibrium with aldehyde 2; 3. Aldehyde 2 reacts with ylide 1 to form oxaphosphetane 3; 4. Oxaphosphetane 3 expels triphenylphosphine oxide to form alkene 4 (the alkene is primarily formed in the desired Z configuration); 5. Alkene 4 is oxidized with PCC to form aldehyde 5; 6. Alkyl bromide 1 reacts with magnesium and ether to form Grignard reagent 6; 7. Grignard reagent 6 adds to aldehyde 5 to form tetrahedral intermediate 7; 8. Tetrahedral intermediate 7 reacts with dilute aqueous acid to form alcohol 8; 9. Alcohol 8 is oxidized with chromic acid to yield (Z)-6-Heneicosene-11-one. Diagram these steps on a separate sheet of paper, and then draw the structure of oxaphosphetane 3. • 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. (Z)-6-Heneicosene-11-one
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
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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.
Several syntheses of this compound have been reported, one of which is shown:
O. _OH
Br
(Z)-6-Heneicosene-11-one
alkyl bromide 1
hemiacetal 1
alkyl bromide 2
Br
This synthesis involves the following steps:
1. Alkyl bromide 2 reacts with triphenylphosphine and butyllithium to form ylide 1;
2. Hemiacetal 1 is in equilibrium with aldehyde 2;
3. Aldehyde 2 reacts with ylide 1 to form oxaphosphetane 3;
4. Oxaphosphetane 3 expels triphenylphosphine oxide to form alkene 4 (the alkene is primarily formed in the desired Z configuration);
5. Alkene 4 is oxidized with PCC to form aldehyde 5;
6. Alkyl bromide 1 reacts with magnesium and ether to form Grignard reagent 6;
7. Grignard reagent 6 adds to aldehyde 5 to form tetrahedral intermediate 7;
8. Tetrahedral intermediate 7 reacts with dilute aqueous acid to form alcohol 8;
9. Alcohol 8 is oxidized with chromic acid to yield (Z)-6-Heneicosene-11-one.
Diagram these steps on a separate sheet of paper, and then draw the structure of oxaphosphetane 3.
• 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.
(Z)-6-Heneicosene-11-one
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