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Magazine Chapter 9: Q13P (page 480)
The fragrance of (Z)-1-phenylhex-2-en-1-ol resembles that of roses, with a delicate citrus edge. Show how you would synthesize this compound from benzaldehyde (PhCHO) and any other reagents you need.
Short Answer
The mechanism goes as:
Step by step solution
Partial catalytic hydrogenation of alkyne
Some reagents like platinum, palladium, and nickel do catalytic hydrogenation, which converts alkyne to an alkane.
To restrict the conversion of alkyne to an alkane, some reagents like Lindlar鈥檚 catalyst and metal-ammonia are used, which stops the conversion of alkene to alkane. The process is called partial hydrogenation of alkyne.
Synthesis of (Z)-1-phenylhex-2-ene-1-ol from benzaldehyde and other reagents.
Sodium amide (base) takes the proton from pentyne (terminal carbon) to form a carbanion (propyl acetylide).
Later, adding propyl acetylide to benzaldehyde (protonated in presence of acid) forms alcohol as shown below. The hydrogen atom that protonates oxygen, increases the electrophilicity of carbon in benzaldehyde.
Finally, hydrogen in the presence of Lindlar鈥檚 catalyst, one can obtain the final product (Z)-1-phenylhex-2-ene-1-ol.
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