Which of the following products (citronellal, geraniol, nerol, and/or epoxycitra

Question

Which of the following products (citronellal, geraniol, nerol, and/or epoxycitral) would result from the following reaction process: If you can please show visually how the reaction occurs between the reactants to form whichever product goes with each reaction. Appreciate it!

REACTION 1:

To a vial add citral (25 L, 0.15 mmol) and anhydrous THF (1 mL). Then add the Hantzsch ester (40 mg, 0.16 mmol, 1.1 equiv.) and dibenzylammonium trifluoroacetate (7 mg, 0.02 mmol). Cap the vial, swirl gently if desired, and allow the mixture to react at room temperature for 1-7 days. Monitor reaction progress by TLC, comparing with authentic standards. To work up the reaction, add 1 mL deionized water and extract with dichloromethane (3 x 1 mL). Dry the combined organic layers with sodium sulfate and decant into a tared flask. Concentrate under reduced pressure to obtain the crude product.

Explanation / Answer

Synthesis

The above shown synthetic reduces selectively the C=C alkene double bond while retaining any carbonyl functionality in the starting material.

Therefore, the above synthetic strategy would yield, "citronellal" as the product wherein, the double bond is reduced but the aldehyde group remains as it is.

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