Question

Lab : Aldol Condensation

Purpose.  In this lab you will conduct the Aldol condensation reaction under solid-state reaction conditions that will involve grinding reactants in the solid phase. You must read ahead and learn about this reaction and the chemical mechanism for the Aldol condensation. There are two possible products which are the initial Aldol or subsequent elimination product. You will need to isolate and purify your reaction product.  You will use your melting point, IR, ¹H and ¹³C NMR spectra to determine the structure of your product.

Table of Reagents. Synthesis experiments require a table with the first column listing the Chemical Name of all reagents, roughly in the order in which they are used in the experimental procedure. That is followed by a column with the Chemical Formula, and a column of the “Purpose” of the reagent (i.e., reactant, drying agent, solvent, etc.).  For everything you identified as “Reactant”, “Product”, or “Solvent”, you will also need columns for: structure, molecular weight, and physical properties (melting point, boiling point, density).  Copy the sample table below into your notebook, and fill in the required information. Refer back to your previous reagent tables for assistance.

Chemical Name	Purpose	chemical formula	structure	molecular mass (g/mole)	melting point (oC)	boiling point (oC)	density (liquids) (g/mL)
3,4-dimethoxybenzaldehyde						N/A	N/A
1-indanone						N/A	N/A
Sodium hydroxide			N/A	N/A	N/A	N/A	N/A
Hydrochloric acid			N/A	N/A	N/A	N/A	N/A
Ethanol				N/A	N/A	N/A	N/A
Water				N/A	N/A	N/A	N/A
2-(3,4-dimethoxybenzylidene)-indan-1-one	Product	C18H16O3		280.32	183-185	N/A	N/A

1) Goals. Based on your reading, what are the “Experimental Goals” for this experiment?

Common Risk factors in the organic chemistry lab (cross out those that are not applicable to this lab)	What is the associated Hazard? (burn, sharp/cuts, solvent vapor, skin irritant, eye irritant, etc.)	How will you limit Exposure to the hazard?	SDS Section 2 summary	SDS Section 8 summary
Hot plate
Hazardous chemicals
Strong acids and/or bases
Volatile solvents
Glassware
Melting point capillary tube
Electrical equipment
Vacuum filtration
InfraRed Light
1-indanone: Health & Safety (look up SDS at Flinn website)

3) Reaction Equation.  Sketch the full reaction from the handout in your notebook (mechanism not required).

4) In your reaction equation circle the CH₂group in the initial Aldol product and in the final elimination product. Then write down the type of splitting pattern you would predict for the CH₂group in each of the two products.

5) We may have not yet covered the Aldol condensation in class.  Look up “base catalyzed Aldol condensation” and write a concise paragraph that describes (a) the reaction, (b) the meaning of an enol and enolate, and (c) the importance of this reaction in organic chemistry.  

Answer 1