Organic Chemistry Lab 1 Final Study Guide

Flashcard maker : Lily Taylor
Simple Distillation
Reflux
Reflux is a distillation technique involving the condensation of vapors and the return of this condensate to the system from which it originated.
Liquid-Liquid Extraction
What process is used to isolate all organic compounds that were forced into the the aqueous phase when water was added. Between 2 immiscible solvents.
Recrystallization
Purification of a solid. By dissolving both impurities and a compound in an appropriate solvent, either the desired compound or impurities can be coaxed out of solution, leaving the other behind. It is named for the crystals often formed when the compound precipitates out.
Vaporization
The process of turning a liquid into a vapor
Condensation
Turning a vapor into a liquid
Steam Distillation
Natural products are often isolated from raw materials
Fractional Distillation
Liquids which boil below 150 degrees Celsius at 1 atm of pressure and have boiling points less than 25 0C apart would be separated
What solvent should NEVER be use to clean a salt plate for IR spectroscopy?
Water
Mass Spectrometry
Analysis technique used to determine the molecular weight of a compound
Separation/Purification Techniques:
1.) Recrystallization
2.) Distillation
3.) Extraction
4.) Column Chromatography
5.) Filtration
NMR
Nuclear Magnetic Resonance Spectroscopy. Analysis technique that gives information on the carbon-hydrogen framework of a molecule.
Assuming you have set up a correct vertical reflux condenser, the cool water outlet will be the ______________ inlet.
Top
After the ester hydrolysis reaction is complete, how do you separate the alcohol from the reaction mixture?
Simple Distillation
Saponification
Term used for base promoted hydrolysis
The reflux temperature is near the boiling point of the _____.
Solvent
Azeotrope
Ethyl alcohol and water are known to form a 96%-4% mixture which boils at a constant temperature (lower than the boiling point of either component in its pure form). This is a two component system that distills at a constant temperature.
The ideal solvent for the recrystallization of a particular compound is one that:
1.) Boils at a temperature below the compound’s melting point.
2.) Dissolves a moderately large amount of the compound when hot.
3.) Does not react with the compound.
4.) Dissolves only a small amount of compound when cool.
When two imiscible liquids are placed in a separatory funnel, the liquid with the lower density will form the __________ layer.
Top
Vacuum Filtration
A specific technique used to separate solid material from a solution.
Instead of two distinct layers, sometimes a fog of particles forms in a separatory funnel and is known as an _______.
Emulsion
In a CRC Handbook of Chemistry and Physics, the melting point of a compound is sometimes reported as a single number. What does this mean?
It’s the upper limit of the melting point range.
The melting point of a pure organic compound:
is sharp, having a range of 1 degree or less.
Each component of a fractional distillation that is collected is known as a _______.
Fraction
All of the steps in the fractional distillation process are
___________ steps.
Equilibrium
A compound with a lower boiling point will have a _____________ retention time on a GC column than a compound with a higher boiling point.
Shorter
The gas chromatography setup we will be using in this experiment (Dehydration of 2-Methylcyclohexanol) separates compounds based on their __________.
Boiling points
The printout you will receive from the GC is a plot of
_________ vs. ________ time.
Peaks, retention
Which of the following qualitative organic functional group tests will we be performing to test for the presence of C=C double bonds?
Br2 in chloroform Test and KMnO4 Test
According to Zaitsev rule what do you expect as a major product as a result of dehydration of 2-methylcyclohexan-1-ol ?
1-methylcyclohexene or 3-methylcyclohexene?
1-methylcyclohexene
What rule can we use before analyzing our GC plot to determine which of the possible alkene products should be the major product?
Zaitsev’s Rule
The bromine solution is reddish-orange. Bromine reacts with an alkene to form a ———— solution.
Colorless
When any of the possible alkylhalide products of the reaction are mixed with water in a separatory funnel, which layer will be the organic layer?
Bottom
Electrophile
Electron poor species
Nucleophile
Electron rich species
Primary Alcohols reacts via ______.
Sn2
Secondary Alcohols reacts via _______.
Sn2 and Sn1
IR
Determines functional groups in a compound.
GC
Determines # and % of components in a sample.
Whether a reaction will proceed via an SN1 or an SN2 process depends on:
The structure of the reactants and the reaction conditions.
When any of the alkylhalide products are mixed with 9M sulfuric acid in a separatory funnel, which layer will be the organic layer?
Top
Last week you carried out 4 extractions of your crude product. What was the purpose of the extraction with 9M H2SO4?
To remove any unreacted alcohol from the distillate.
The overall reaction of an alcohol with sodium bromide to produce an alkyl bromide and water is an example of:
A nucleophilic substitution reaction.
Zaitsev’s Rule
The major product is the more stable product with the more substituted double bond.
The KMnO4 is purple. It reacts with an alkene to form:
A colorless solution with a brown MnO4 precipitate.
Synthesis of an alkyl halide lab:
Purpose was to synthesize an alkyl bromide from an unknown primary or secondary alcohol.
Week 1: NaBr, di water and the unknown was mixed, and sulfuric acid was added drop wise via the column, turning yellow at the end. Reflux was started and ran for 30 minutes. The solution was then cooled, and simple distillation was ran. The samples were combined with a partner and washed with di water, organic layer collected.Tthen washed with H2So4, then 10 ml of di water, then CaCO3.
Week 2: sample was poured through a plugged buchner funnel and put through simple distillation. Mass and volume collected for density. IR, GC, & NMR was ran.
Dehydration of 2-Methylcyclohexan-1-ol lab:
Week 1: fractional distillation of an unknown alcohol and phosphoric acid. Distillate was then added to seperatory funnel, and washed with sodium bicarbonate. Water removed and organic layer was washed with sodium bicarbonate again. CaCl2 was added to organic layer, and corked for the next week.
Week 2: the liquid was decanted off and put through simple distillation. GC was ran, Br2 and KMnO4 test were ran to determine the presence of double bonds.

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