How many molecules of vanillin can NaBH4 reduce?

How many molecules of vanillin can NaBH4 reduce?

In theory, one equivalent of NaBH4 could reduce four equivalents of vanillin since all four of the hydrides could react. Nevertheless, it is very common to use a stoichiometric (or near-stoichiometric) amount of NaBH4 since the rate of hydride transfer decreases significantly as more alkoxy groups are added to boron.

Is vanillin and sodium borohydride the limiting reagent?

the purpose is to be able to conduct the reduction reaction of vanillin using NaBH4. Which compound (vanillin or sodium borohydride) is the limiting reagent? Vanillin is the limiting reagent. Assuming you use 2.5g vanillin and 5.0 mL of a 3.42 M NaBH4 solution, what is the theoretical yield of vanillyl alcohol.

What is the mole ratio of NaBH4 to vanillin in the reaction?

According to the collision theory, the concentration of when more amount of NaBH4 reacts, the chance of collisions between BH4-ions and vanillin molecules is higher. 4:1 ratio is the original reaction stoichiometry.

How does sodium borohydride reduce?

SODIUM BOROHYDRIDE Reduces aldehydes and ketones to corresponding alcohols. Sodium borohydride is not reactive to esters, epoxides, lactones, carboxylic acids, nitro compounds and nitriles, but reduces acyl chlorides.

Why is NaOH used to dissolve vanillin?

The reason for dissolving our Vanillin in NaOH is because we wanted to deprotonate the the “OH” on the Phenol so that when we add the NaBH4, the hydride can attack the carbonyl group and not the hydrogen on the “OH “and from H2 gas. Sodium borohydride reduces the aldehyde group in vanillin to primary alcohol.

What is the equivalent of NaBH4?

Practically speaking, a chemist will use one equivalent of sodium borohydride to reduce an aldehyde or ketone. However, theoretically only 0.25 equivalents are necessary. Borohydride donates a hydride to the carbonyl carbon, generating borane, which is a weaker reducing agent than borohydride.

What is the limiting reagent in reduction of vanillin?

From 1 mole of vanillin the equal amount of moles vanillyl alcohol can be produced. The limiting reagent here is vanillin because there is 0.5 mol NaBH4 which is more than enough to reduce all vanillin. So, theoretical yield of vanillyl alcohol will be also 0.001 mol.

What is the function of sodium borohydride?

Sodium borohydride (NaBH4) is a reagent that transforms aldehydes and ketones to the corresponding alcohol, primary or secondary, respectively.

How does sodium borohydride react with water?

Chemical hydrides such as sodium borohydride (NaBH4), release hydrogen via exothermic reaction with water as follows: NaBH4 + (2+x) H2O → 4H2 + NaBO2·xH2O + heat. A value of x greater than zero corresponds to unused water, which incurs a gravimetric and volumetric penalty on the storage system.

Does vanillin dissolve in NaOH?

Vanillin is mostly insoluble in water but soluble in aqueous sodium hydroxide solution? What did you add to make the vanillin dissolve and explain why it dissolves. What four purposes did aqueous hydrochloric acid serve in the reduction of vanillin to vanillyl alcohol?

Why is NaBH4 used in excess?

NaBH4 is a very effective and selective reducing agent. This is the main reason why a slight excess of sodium borohydride is used customarily in reduction reactions. NaBH4 is above all used for reducing aldehydes and ketones. Aldehydes can be reduced selectively in the presence of ke- tones.

What is the equivalent of sodium borohydride?

How to reduce vanillin with sodium borohydride?

The overall, balanced equation for this reaction is given in equation (3); it is balanced with respect to the key reactants, vanillin, 1, and sodium borohydride, and the product, vanillyl alcohol, 2. EXPERIMENTAL OVERVIEW In this experiment, you will use sodium borohydride to reduce the aldehyde functional group in Vanillin.

How is vanillin reduced by NaBH4 in aqueous solution?

The mechanism for the reduction of vanillin by NaBH4 a) Using pure water instead of sodium hydroxide would decompose the reagent since it is in an aqueous solution and not stable at a neutral or acidic pH. Hydrogen gas would be produced similar to what occurs in the experiment from addition of HCl with the excess NaBH4.

How did they reduce vanillin to vanillyl alcohol?

The experiment attempted to reduce vanillin to vanillyl alcohol using a reduction reaction with sodium borohydride. The reduction reaction was completed in a base medium with NaOH because an acidic medium such as H3O+ would take a proton from NaBH4 and NaBH4 would decompose from interacting with the acid.

How to measure selectivity in vanillin acetate reduction?

In this experiment, the reduction of vanillin acetate using sodium borohydride was explored. The reaction was monitored using thin-layer chromatography, and the product was identified using infrared, H-NMR, and C-MNR spectroscopies.