Question

1) Write a mechanism for the reduction of vanillin by sodium borohydride under the reaction conditions you used. 2) Write a balanced equation for the decomposition of sodium borohydride in water to which HCl has been added. 3) Describe and explain the possible effect on your results of the following experimental errors or variations during the synthesis of vanillyl alcohol: a) You used pure water as the reaction solvent b) You used 5 mL of 1M NaOH for the NaBH4 solution and 10 mL of 1M NaOH for the vanillin solution c) Because you started with 25 mmol of vanillin, you assumed that a 100% excess of NaBH4 was 50 mmol and used that amount. 4) Draw the structure of the product you would have obtained if you had used NaBD4 as the reducing agent. Justify you answer. (D = deuterium, an isotope of hydrogen). 5) Draw a separation/purification flow diagram. Note: It should include the steps where you purified your product, and where the impurities were eliminated from the product.

          1) Write a mechanism for the reduction of vanillin by sodium borohydride under the reaction
conditions you used.

2) Write a balanced equation for the decomposition of sodium borohydride in water to which
HCl has been added.

3) Describe and explain the possible effect on your results of the following experimental errors
or variations during the synthesis of vanillyl alcohol:

a) You used pure water as the reaction solvent
b) You used 5 mL of 1M NaOH for the NaBH4 solution and 10 mL of 1M NaOH for the
vanillin solution
c) Because you started with 25 mmol of vanillin, you assumed that a 100% excess of
NaBH4 was 50 mmol and used that amount.

4) Draw the structure of the product you would have obtained if you had used NaBD4 as the
reducing agent. Justify you answer. (D = deuterium, an isotope of hydrogen).

5) Draw a separation/purification flow diagram. Note: It should include the steps where you
purified your product, and where the impurities were eliminated from the product.

1) Write a mechanism for the reduction of vanillin by sodium borohydride under the reaction
conditions you used.

2) Write a balanced equation for the decomposition of sodium borohydride in water to which
HCl has been added.

3) Describe and explain the possible effect on your results of the following experimental errors
or variations during the synthesis of vanillyl alcohol:

a) You used pure water as the reaction solvent
b) You used 5 mL of 1M NaOH for the NaBH4 solution and 10 mL of 1M NaOH for the
vanillin solution
c) Because you started with 25 mmol of vanillin, you assumed that a 100% excess of
NaBH4 was 50 mmol and used that amount.

4) Draw the structure of the product you would have obtained if you had used NaBD4 as the
reducing agent. Justify you answer. (D = deuterium, an isotope of hydrogen).

5) Draw a separation/purification flow diagram. Note: It should include the steps where you
purified your product, and where the impurities were eliminated from the product.

Added by Eduardo M.

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