Tuesday, November 26, 2013

Exploring Conformational Analysis using Molecular Models

1. Draw the molecule methane using the wedge and dash depiction

2.      Draw ethane in wedge and dash depiction, sawhorse depiction and in its Newman projection. Show both eclipsed and anti forms.
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3.      Draw butane in wedge and dash depiction, sawhorse depiction and in its Newman projection looking down the 2,3 bond. Show eclipse, gauche and anti forms.
 
 
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4.      Draw all Newman projections of 2-methylhexane showing eclipsed, gauche and anti forms. Rotate about the 3,4 carbon-carbon bond and watch what happens to the groups. Draw a potential energy diagram for the rotation about the 3,4 carbon-carbon bond plotting Potential Energy versus Torsion Angle.
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5.      Draw cyclopropane and cyclobutane in three dimensions, be sure to include the hydrogen atoms.
Cyclopropane
Cyclobutane
 
 
6.       Draw the chair form of cyclohexane.
 

7.       Draw the following molecules twice, once using the chair conformation AND once using the wedge and dash depiction.

1,2 cis-dimethylcyclohexane

1,2 trans-dibromocyclohexane

1,3 cis-dichlorocyclohexane

1,3 trans-dimethylcyclohexane

1,4 cis-dimethylcyclohexane

1,4 trans-dibromocyclohexane
 
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Tuesday, November 13, 2012

How to fill a melting point capillary

First, be sure that you have the right capillary for the machine you are going to use. There are two different mp machines in the lab. One is digital and uses slightly smaller capillaries than the older machines. If you force the old, larger capillaries into the new machine, they will get stuck and will take the new digital mp’s out of service. Please be careful.

Please the opened end of the capillary onto the pile of crystals. The closed end should be pointing up. The crystals will be held in the tube.
fill a melting point capillary

fill a melting point capillary

Turn the tube right side up and tap on the bench top. The crystals will fall to the closed end of the capillary.

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Identification and Characterization of an Unknown Solid Using Melting Point and Mixes MP

YOUR SAMPLE FROM THE RECRYSTALLYZATION EXPERIMENT will be analyzed by melting point and mixed melting point. A sample must be dry (free of solvent) before an accurate melting point can be established.

Melting point may be used to determine the purity of a compound based on its melting range or to determine the identity of an unknown given a source of known compounds. An impure compound melts lover than expected and has a larger than two degree range. A higher mp indicates a completely different compound may be present.

The melting point of a solid is really a melting range, the sample should be heated at 1-2 degrees of Celsius  / min. the first drop of liquid is the start if the range and the temperature at which total melting occurs is the upper limit of the range. It is best to take two melting points of an unknown; a quick melting point with heating 5-10 degrees of Celsius / min to get in the area of the real mp. The second, more accurate mp, should be done slowly at 1-2 degrees of Celsius / min per near the mp. Use a new sample each time and be sure the apparatus has cooled to below the mp between runs. The sample cannot be reused because decomposition may have taken place during the first heating. The sample is placed in a capillary tube with one end closed. Fill with about 2-3 mm of crystals. Place the open end of the capillary over the crystals and push onto the crystals. Then turn the capillary over and tap on the lab bench until the crystals fall to the closed end.

When you have an idea of the identity of your compound you should carry out a mixed melting point with the authentic material that is available in the laboratory. To do this, mix a small amount of your unidentified material with the same amount of known material. Determine the mp of the mixture. Of the two compounds are the same, there should be no change in melting point.

However, if the unknown is something else, you will see a depressed mp with a broader range. Why? Try using the wrong compound intentionally. Simply comparing the mp of an unknown with the literature value is incomplete evidence to identify an unknown. Many organic compounds have identical melting points.

You will determine many melting points throughout the semester. Be sure you understand the technique now. Always make sure youy compound is dry (free of water) and free of solvent before putting it in the mp capillary. It will not dry in the capillary and you will get erroneous results.

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Thursday, November 1, 2012

Melting Pints of Some Organic Compounds

Compound name                                                                                   MP(in degrees of Celsius)
acetanilide                                                                                                        113-115
p-nitrobenzaldehyde                                                                                         106-108
benzoic acid                                                                                                     122-123
acetylsalicylic acid                                                                                           138-140
4-dimethylaminobenzaldehyde                                                                          73-75
4-hydroxy-3-methoxybenzaldehyde (also known as vanillin)                           81-83
salicylic acid                                                                                                    159-160
p-aminoacetanilide                                                                                          162-163
o-toluic acid                                                                                                     103-105
p-toluic acid                                                                                                     180-182
m-toluic acid                                                                                                    108-110
p-toluic acid                                                                                                     180-182
3-nitroaniline                                                                                                   112-114
o-aminobenzoic acid                                                                                       144-148
m-aminobenzoic acid                                                                                      178-180
t-cinnamic acid                                                                                                134-135
o-nitrobenzoic acid                                                                                          146-148
m-nitrobenzoic acid                                                                                         139-141
p-nitrobenzoic acid                                                                                          237-240

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Wednesday, October 31, 2012

Be familiar with your glassware Beaker (Conical flask/ erlenmeyer flask, Glass rod with policeman, Short stem funnel, Watch glass, Filter paper, Activated carbon, Hot plates, Stand and ring support)

Be familiar with your glassware

 Beaker



 











Conical flask/ erlenmeyer flask


 











 Glass rod with policeman

 












 Short stem funnel



 








  

Watch glass



 










Other things you will need for this experiment





Filter paper


 









 Activated carbon
 




 









 Hot plates

 

 








 Stand and ring support



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