i need to caluclate a rf value for the tlc plate and i really need help with showing the steps please! Reduction of 4-Nitrobenzaldehyde to 4-Nitrobenzyl Alcohol and Thin Layer Chromatography A = 4-nitrobenzaldehyde (starting material)B = bothC = 4-nitrobenzyl alcohol (product)AB. After the reaction has been completed, add about 20 mL of methylene chloride(dichloromethane/ DCM), and pour the solution into a separatory funnel. Add 20 mL ofwater to the separatory funnel. Shake and let the aqueous and organic layers separate.Place the organic layer (which layer is that?) with your product in an Erlenmeyer flask.Repeat with another portion of methylene chloride. Combine the organic layers and add adrying agent. Gravity filter the solution into 100 mL pre-weighed round-bottom flask andwash the flask and drying agent with an additional 5mL of methylene chloride, alsofiltered into your round bottom flask. Evaporate the solvent on a steam bath in the hood(Erlenmeyer), or use the rotary evaporator (round bottom flask). Weigh the flask againand calculate the crude yield.(Be sure all solvent has been removed!)Purification by recrystallization. Take a melting point of your crude product. Read thesection on recrystallization in your lab text before you come to class. Recrystallization isa technique for purification of a solid compound. In general, the compound (and anyimpurities) is dissolved in a minimal volume of hot solvent (or solvent mixture). This hotsolution is left to cool slowly to room temperature, and then placed in an ice bath. Thesolubility of compounds is less in colder solutions, so crystals of compound should formslowly from the saturated solution. (Since the impurity should be present in smallquantities, the impurity will stay in solution while the compound of interest iscrystallizing). If crystal formation is slow enough, the crystal should be pure compound.The purified compound is physically separated from solution by filtration. However, ifthis crystal formation is fast, impurities may be trapped in the rapidly forming lattice ofthe solid crystal. Therefore, it is important to be patient while performing arecrystallization.It may help you to see pictures of a movie of theprocess.Recrystallize the product from methylene chloride, and determine the weight percentagerecovery for this purification step once this purified solid has completely dried. If yourTLC of CP1 or CP2 contained multiple spots, take a TLC of the purified compound bydissolving a few crystals in methylene chloride and eluting with the same solvent asabove (30% ethyl acetate; 70% petroleum ether). Mark this purified product PP.

TLC can easily tell whether a reaction is complete or not. On a TLC plate, a polar compound takes…

i need to caluclate a rf value for the tlc plate and i really need help with showing the steps please! Reduction of 4-Nitrobenzaldehyde to 4-Nitrobenzyl Alcohol and Thin Layer Chromatography

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter12: Unsaturated Hydrocarbons

Section: Chapter Questions

Problem 12.29E: What is an important commercial application of hydrogenation?

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Reduction of 4-Nitrobenzaldehyde to 4-Nitrobenzyl Alcohol and Thin Layer Chromatography

A = 4-nitrobenzaldehyde (starting material)
B = both
C = 4-nitrobenzyl alcohol (product)
A
B.

After the reaction has been completed, add about 20 mL of methylene chloride
(dichloromethane/ DCM), and pour the solution into a separatory funnel. Add 20 mL of
water to the separatory funnel. Shake and let the aqueous and organic layers separate.
Place the organic layer (which layer is that?) with your product in an Erlenmeyer flask.
Repeat with another portion of methylene chloride. Combine the organic layers and add a
drying agent. Gravity filter the solution into 100 mL pre-weighed round-bottom flask and
wash the flask and drying agent with an additional 5mL of methylene chloride, also
filtered into your round bottom flask. Evaporate the solvent on a steam bath in the hood
(Erlenmeyer), or use the rotary evaporator (round bottom flask). Weigh the flask again
and calculate the crude yield.
(Be sure all solvent has been removed!)
Purification by recrystallization. Take a melting point of your crude product. Read the
section on recrystallization in your lab text before you come to class. Recrystallization is
a technique for purification of a solid compound. In general, the compound (and any
impurities) is dissolved in a minimal volume of hot solvent (or solvent mixture). This hot
solution is left to cool slowly to room temperature, and then placed in an ice bath. The
solubility of compounds is less in colder solutions, so crystals of compound should form
slowly from the saturated solution. (Since the impurity should be present in small
quantities, the impurity will stay in solution while the compound of interest is
crystallizing). If crystal formation is slow enough, the crystal should be pure compound.
The purified compound is physically separated from solution by filtration. However, if
this crystal formation is fast, impurities may be trapped in the rapidly forming lattice of
the solid crystal. Therefore, it is important to be patient while performing a
recrystallization.
It may help you to see pictures of a movie of the
process.
Recrystallize the product from methylene chloride, and determine the weight percentage
recovery for this purification step once this purified solid has completely dried. If your
TLC of CP1 or CP2 contained multiple spots, take a TLC of the purified compound by
dissolving a few crystals in methylene chloride and eluting with the same solvent as
above (30% ethyl acetate; 70% petroleum ether). Mark this purified product PP.

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