Background InformationIn a 125 mL Erlenmeyer flask, dissolve 25.0 mmol of vanillin in 30 mL 1 M sodium hydroxide. If the mixture does not dissolve after 5 minutes of continuous stirring, add another 5 mL sodium hydroxide. Cool the solution to just below 15°C. In a small beaker, dissolve 12.0 mmol of sodium borohydride in about 6 mL of 1 M sodium hydroxide.Remove the vanillin solution from the ice bath and add the sodium borohydride solution in small portions to the vanillin over a 5-minute period. Over time, the reaction mixture will warm up. Keep the temperature within the range of 20-25°C. If it is too cool, the reaction will proceed too slowly. If it is too warm, the product will not crystallize properly in the end. Once all of the sodium borohydride has been added, let the solution sit for 30 minutes, with frequent swirling.Once the 30 minutes have elapsed, place the reaction mixture in an ice bath, cooling it to below 20°C. Acidify the solution with 6 M hydrochloric acid (6-10 mL may be required), keeping the temperature low. Perform this step carefully to prevent the temperature from spiking, but quickly enough so that “foaming” is observed. Once the yellow color has faded, check the pH with litmus paper to ensure that the mixture is acidic. Crystallization should have occurred during the neutralization process. If it has not, it may be necessary to seed the solution with crystals from another student. After neutralization is complete, ice the reaction mixture for 15 minutes prior to filtration.Collect the vanillyl alcohol by vacuum filtration and wash the crystals with cold water. Store the product in a container specified by the instructor until next week. Once the sample has dried, determine its mass and melting point. Clean up and waste disposal: QuestionsIf you were to follow the progress of this reaction using IR spectroscopy, you would see Disappearance of a broad peak above 3000cm-1 Disappearance of a peak around 1700cm-1 Disappearance of a broad peak above 3000cm-1 and appearance of peak around 1700cm-1 Disappearance of a peak above 1700-cm1 and appearance of a broad peak around 3000cm-1QUESTION 2If you were following this reaction using Mass spec, a strong peak at M/z of 28 would indicate: Complete conversion of the reactant to product possible side reactions presence of unreacted aldehyde a high yielding reactionQUESTION 3If the proton NMR showed a singlet and 2 doublets clustered between 7-8ppm. You can infer that: The conversion from aldehyde to alcohol was incomplete there was no reaction does not provide any information regarding the success of the reaction. The reaction was high yielding.QUESTION 4The limiting reagent in this experiment is vanilla vanillin sodium borohydride sodium hydroxideQUESTION 5The gas evolved in this reaction is carbon dioxide nitrogen oxygen HydrogenQUESTION 6Reduction reaction involves Addition of hydrogens removal of hydrogens addition of oxygens removal of H+QUESTION 7Theoretically, one mole of sodium borohydride can react with _______moles of vanilin 4 3 2 5QUESTION 8Care has to be taken to keep the reaction mixture at _________during the addition of HCl. 55 deg 25 deg 0 deg 15 degQUESTION 9Sodium borohydride reduces___________ and ____________ but not _____________ aldehydes and ketones not esters aldehydes and esters not ketones alkanes and ketones not aldehydes aldehydes and ketones CompoundWeight (g)Melting Point (C)Vanillin (starting3.881-83material)Vanillin Alcohol2.619113(product)Sodium Borohydride0.452400

Question

Background InformationIn a 125 mL Erlenmeyer flask, dissolve 25.0 mmol of vanillin in 30 mL 1 M sodium hydroxide.  If the mixture does not dissolve after 5 minutes of continuous stirring, add another 5 mL sodium hydroxide.  Cool the solution to just below 15°C.  In a small beaker, dissolve 12.0 mmol of sodium borohydride in about 6 mL of 1 M sodium hydroxide.Remove the vanillin solution from the ice bath and add the sodium borohydride solution in small portions to the vanillin over a 5-minute period. Over time, the reaction mixture will warm up. Keep the temperature within the range of 20-25°C.  If it is too cool, the reaction will proceed too slowly. If it is too warm, the product will not crystallize properly in the end.  Once all of the sodium borohydride has been added, let the solution sit for 30 minutes, with frequent swirling.Once the 30 minutes have elapsed, place the reaction mixture in an ice bath, cooling it to below 20°C. Acidify the solution with 6 M hydrochloric acid (6-10 mL may be required), keeping the temperature low.  Perform this step carefully to prevent the temperature from spiking, but quickly enough so that “foaming” is observed.  Once the yellow color has faded, check the pH with litmus paper to ensure that the mixture is acidic. Crystallization should have occurred during the neutralization process. If it has not, it may be necessary to seed the solution with crystals from another student. After neutralization is complete, ice the reaction mixture for 15 minutes prior to filtration.Collect the vanillyl alcohol by vacuum filtration and wash the crystals with cold water. Store the product in a container specified by the instructor until next week. Once the sample has dried, determine its mass and melting point. Clean up and waste disposal:  QuestionsIf you were to follow the progress of this reaction using IR spectroscopy, you would see  Disappearance of a broad peak above 3000cm-1  Disappearance of a peak around 1700cm-1  Disappearance of a broad peak above 3000cm-1 and appearance of peak around 1700cm-1  Disappearance of a peak above 1700-cm1 and appearance of a broad peak around 3000cm-1QUESTION 2If you were following this reaction using Mass spec, a strong peak at M/z of 28 would indicate:  Complete conversion of the reactant to product  possible side reactions  presence of unreacted aldehyde  a high yielding reactionQUESTION 3If the proton NMR showed a singlet and 2 doublets clustered between 7-8ppm. You can infer that:  The conversion from aldehyde to alcohol was incomplete  there was no reaction  does not provide any information regarding the success of the reaction.  The reaction was high yielding.QUESTION 4The limiting reagent in this experiment is  vanilla  vanillin  sodium borohydride  sodium hydroxideQUESTION 5The gas evolved in this reaction is  carbon dioxide  nitrogen  oxygen  HydrogenQUESTION 6Reduction reaction involves  Addition of hydrogens  removal of hydrogens  addition of oxygens  removal of H+QUESTION 7Theoretically, one mole of sodium borohydride can react with _______moles of vanilin  4  3  2  5QUESTION 8Care has to be taken to keep the reaction mixture at _________during the addition of HCl.  55 deg  25 deg  0 deg  15 degQUESTION 9Sodium borohydride reduces___________ and ____________ but not _____________  aldehydes and ketones not esters  aldehydes and esters not ketones  alkanes and ketones not aldehydes  aldehydes and ketones CompoundWeight (g)Melting Point (C)Vanillin (starting3.881-83material)Vanillin Alcohol2.619113(product)Sodium Borohydride0.452400

Accepted Answer

Since you have asked a question with multiple sub-parts, we will solve first three sub-parts for…

		Disappearance of a broad peak above 3000cm^-1
		Disappearance of a peak around 1700cm^-1
		Disappearance of a broad peak above 3000cm^-1 and appearance of peak around 1700cm^-1
		Disappearance of a peak above 1700^-cm¹ and appearance of a broad peak around 3000cm^-1

		Complete conversion of the reactant to product
		possible side reactions
		presence of unreacted aldehyde
		a high yielding reaction

		The conversion from aldehyde to alcohol was incomplete
		there was no reaction
		does not provide any information regarding the success of the reaction.
		The reaction was high yielding.

		Addition of hydrogens
		removal of hydrogens
		addition of oxygens
		removal of H⁺

		aldehydes and ketones not esters
		aldehydes and esters not ketones
		alkanes and ketones not aldehydes
		aldehydes and ketones