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The chemical compound used in this experiment as the reducing agent is the Sodium Borohydride. (NaBH4) 5. Refer to the reaction stoichiometry Lehman pp. 55. Write by hand a balanced chemical equation using the structures of camphor and isoborneol. Then, Calculate the theoretical yield of the chemical reaction from above when 0.2575 g camphor and 0.2179 g sodium borohydride were used.

The chemical compound used in this experiment as the reducing agent is the Sodium Borohydride. (NaBH4) 5. Refer to the reaction stoichiometry Lehman pp. 55. Write by hand a balanced chemical equation using the structures of camphor and isoborneol. Then, Calculate the theoretical yield of the chemical reaction from above when 0.2575 g camphor and 0.2179 g sodium borohydride were used.

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Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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The chemical compound used in this experiment as the reducing agent is the Sodium Borohydride. (NaBH4) 5. Refer to the reaction stoichiometry Lehman pp. 55. Write by hand a balanced chemical equation using the structures of camphor and isoborneol. Then, Calculate the theoretical yield of the chemical reaction from above when 0.2575 g camphor and 0.2179 g sodium borohydride were used.
Transcribed Image Text:The chemical compound used in this experiment as the reducing agent is the Sodium Borohydride. (NaBH4) 5. Refer to the reaction stoichiometry Lehman pp. 55. Write by hand a balanced chemical equation using the structures of camphor and isoborneol. Then, Calculate the theoretical yield of the chemical reaction from above when 0.2575 g camphor and 0.2179 g sodium borohydride were used.
Borohydride Reduction of Vanillin to Vanillyl Alcohol Sodium borohydride reductions involve nucleophilic addition of hy- dride ion (H:) to the carbonyl carbon, but apparently no free hydride ions are generated. Kinetic evidence suggests that one solvent molecule bonds to the boron atom while it is transferring hydride to the carbonyl com- pound, and another solvent molecule provides a proton to the carbonyl oxygen. H R-OH+0=C +H-B²0- da (R = alkyl or H) B+0-RR- +H-O-C-H+ B -0-C-H This process can continue until all of the hydride ions from BH4 have been used up. Reaction Stoichiometry. The overall stoichiometry of the borohydride reduction of a carbonyl compound is given by the following general equa- tion (R, R' = alkyl, aryl, or H): OH 4RCHR' + H₂BO3 + NaOH 4RCR' + NaBH4 + 4H₂O In practice, it is best to use a 50-100% excess of sodium borohydride to compensate for any that reacts with the solvent or decomposes from other causes. Because the reaction is first order with respect to sodium borohy- dride (as well as the carbonyl compound), using an excess will also increase the reaction rate. Reaction Solvents. Sodium borohydride reductions are usually carried : out in a dilute (~1 M) aqueous NaOH solution or in an alcohol, such as methanol, ethanol, or 2-propanol. The reagent isn't stable at low pH, and even in a neutral aqueous solution it decomposes to the extent of about 4.5% per hour at 25°C. Acidic functional groups, such as COOH and the OH group of a phenol, may cause rapid decomposition of sodium borohy- dride. When a carbonyl compound having such a functional group is being reduced, enough 1 M NaOH should be used to neutralize the functional group and maintain a pH of 10 or higher. Sodium borohydride reacts slowly with alcohols, but ethanol and methanol are usually suitable solvents when there are no acidic functional groups and the reaction time is no more than 30 minutes at 25°C. For longer reaction times or reactions at higher temper- atures, isopropyl alcohol is a better solvent, but it is more difficult to remove after the reaction is over. Reaction Conditions. In most reactions with sodium borohydride, the aldehyde or ketone is dissolved in the reaction solvent and a solution of sodium borohydride is added, with external cooling if necessary, at a rate slow enough to keep the reaction temperature below 25°C. Higher temper- atures may decompose the hydride, and adding the carbonyl compound to the alkaline sodium borohydride solution may cause side reactions of OR + H+ 55
Transcribed Image Text:Borohydride Reduction of Vanillin to Vanillyl Alcohol Sodium borohydride reductions involve nucleophilic addition of hy- dride ion (H:) to the carbonyl carbon, but apparently no free hydride ions are generated. Kinetic evidence suggests that one solvent molecule bonds to the boron atom while it is transferring hydride to the carbonyl com- pound, and another solvent molecule provides a proton to the carbonyl oxygen. H R-OH+0=C +H-B²0- da (R = alkyl or H) B+0-RR- +H-O-C-H+ B -0-C-H This process can continue until all of the hydride ions from BH4 have been used up. Reaction Stoichiometry. The overall stoichiometry of the borohydride reduction of a carbonyl compound is given by the following general equa- tion (R, R' = alkyl, aryl, or H): OH 4RCHR' + H₂BO3 + NaOH 4RCR' + NaBH4 + 4H₂O In practice, it is best to use a 50-100% excess of sodium borohydride to compensate for any that reacts with the solvent or decomposes from other causes. Because the reaction is first order with respect to sodium borohy- dride (as well as the carbonyl compound), using an excess will also increase the reaction rate. Reaction Solvents. Sodium borohydride reductions are usually carried : out in a dilute (~1 M) aqueous NaOH solution or in an alcohol, such as methanol, ethanol, or 2-propanol. The reagent isn't stable at low pH, and even in a neutral aqueous solution it decomposes to the extent of about 4.5% per hour at 25°C. Acidic functional groups, such as COOH and the OH group of a phenol, may cause rapid decomposition of sodium borohy- dride. When a carbonyl compound having such a functional group is being reduced, enough 1 M NaOH should be used to neutralize the functional group and maintain a pH of 10 or higher. Sodium borohydride reacts slowly with alcohols, but ethanol and methanol are usually suitable solvents when there are no acidic functional groups and the reaction time is no more than 30 minutes at 25°C. For longer reaction times or reactions at higher temper- atures, isopropyl alcohol is a better solvent, but it is more difficult to remove after the reaction is over. Reaction Conditions. In most reactions with sodium borohydride, the aldehyde or ketone is dissolved in the reaction solvent and a solution of sodium borohydride is added, with external cooling if necessary, at a rate slow enough to keep the reaction temperature below 25°C. Higher temper- atures may decompose the hydride, and adding the carbonyl compound to the alkaline sodium borohydride solution may cause side reactions of OR + H+ 55
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