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.

Verified step by step guidance

1. Step 1: Begin by identifying the target molecule, (Z)-1-phenylhex-2-en-1-ol. This compound contains a phenyl group attached to a hex-2-en-1-ol backbone with a Z-configuration at the double bond. The starting material is benzaldehyde (PhCHO), which provides the phenyl group.
2. Step 2: Perform a Wittig reaction to introduce the alkene functionality. React benzaldehyde (PhCHO) with a Wittig reagent, such as hexylidene triphenylphosphorane, to form the hex-2-en-1-al intermediate. Ensure that the reaction conditions favor the Z-configuration of the double bond.
3. Step 3: Reduce the hex-2-en-1-al intermediate to the corresponding alcohol, hex-2-en-1-ol. Use a mild reducing agent such as sodium borohydride (NaBH₄) to selectively reduce the aldehyde group without affecting the double bond.
4. Step 4: Verify the stereochemistry of the product to ensure the Z-configuration of the double bond is retained. This can be confirmed using spectroscopic techniques such as NMR or IR.
5. Step 5: Purify the final product, (Z)-1-phenylhex-2-en-1-ol, using techniques such as column chromatography to remove any impurities and isolate the desired compound.

Key Concepts

Aldol Condensation

Aldol condensation is a key reaction in organic chemistry where two carbonyl compounds, typically aldehydes or ketones, react in the presence of a base to form a β-hydroxy aldehyde or ketone. This reaction is crucial for synthesizing larger molecules and can lead to the formation of enones or enals upon dehydration. In the context of synthesizing (Z)-1-phenylhex-2-en-1-ol, an aldol reaction can be employed to create the necessary carbon skeleton from benzaldehyde.

Stereochemistry

Stereochemistry refers to the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In the synthesis of (Z)-1-phenylhex-2-en-1-ol, understanding stereochemistry is essential to ensure the correct geometric isomer is produced, as the 'Z' configuration indicates specific spatial arrangements of substituents around the double bond. This concept is vital for predicting the properties and reactivity of the synthesized compound.

Reduction Reactions

Reduction reactions involve the gain of electrons or the decrease in oxidation state of a molecule, often through the addition of hydrogen or the removal of oxygen. In the synthesis of (Z)-1-phenylhex-2-en-1-ol, a reduction step may be necessary to convert an intermediate carbonyl compound into the corresponding alcohol. Understanding various reducing agents, such as lithium aluminum hydride or sodium borohydride, is important for selecting the appropriate method for achieving the desired product.