Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Microscale Reduction of Cyclohexanone

Read:Chapter 5Chapter 7 (pipet filtering - liquids) pp. 69-70Chapter 15 (for the big picture)Chapter 16 (these are the techniques we will use)Chapter 34 pp 271-276 & 289-293 in the “Survival Guide.”

O OH

NaBH4

CH3OH/CH3O

cyclohexanone cyclohexanol

General Procedure:

Preparation of ProductInto a tared 5.0 mL conical vial weigh 100 :L of cyclohexanone followed by 250:L of methanol. Connect an air condenser to the vial. In the hood, add 300 :Lof the sodium borohydride solution dropwise while swirling occasionally. (Yourinstructor will have previously prepared the sodium borohydride solution.) Take the reaction mixture back to your station and allow the mixture to standfor 15 minutes.

Isolation of ProductUsing a calibrated pipet, add 1.0 mL of dilute HCl (6M) dropwise to the reactionmixture. Extract the product using three 0.5 mL washes of methylene chloride. After separation the methylene chloride is dried by passing the solutionthrough a short Pasteur pipet that contains a small plug of glass wool and thathas about half of the barrel filled with anhydrous sodium sulfate. Themethylene chloride solution is introduced to the top of the drying pipet andallowed to drip into a tared 5.0 mL conical vial that contains a boiling chip. After the solution has eluted from the pipet, an additional 0.5 mL of methylenechloride is passed through the drying pipet and collected in the conical vial. The conical vial is gently heated on a hot plate in the hood to evaporate themethylene chloride.

Analysis of ProductAfter determining the percent yield of the reaction, obtain the infraredspectrum of your product. Compare your spectrum to the provided spectra ofcyclohexanol and cyclohexanone.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.

Discussion Items:

What are the structural differences between cyclohexanol andcyclohexanone?

What are the in the spectra of cyclohexanol and cyclohexanone?How does the spectrum of your product compare to the spectrum of

cyclohexanol?Comment on the purity of your product.