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Reflux is a distillation technique involving the condensation of vapors and the return of this condensate to the system from which it originated.

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Reflux

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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.

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Liquid-Liquid Extraction

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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.

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Recrystallization

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The process of turning a liquid into a vapor

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Vaporization

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Turning a vapor into a liquid

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Condensation

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Natural products are often isolated from raw materials

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Steam Distillation

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Liquids which boil below 150 degrees Celsius at 1 atm of pressure and have boiling points less than 25 0C apart would be separated

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Fractional Distillation

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Water

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What solvent should NEVER be use to clean a salt plate for IR spectroscopy?

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Analysis technique used to determine the molecular weight of a compound

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Mass Spectrometry

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1.) Recrystallization 2.) Distillation 3.) Extraction 4.) Column Chromatography 5.) Filtration

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Separation/Purification Techniques:

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Nuclear Magnetic Resonance Spectroscopy. Analysis technique that gives information on the carbon-hydrogen framework of a molecule.

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NMR

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Top

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Assuming you have set up a correct vertical reflux condenser, the cool water outlet will be the ______________ inlet.

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Simple Distillation

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After the ester hydrolysis reaction is complete, how do you separate the alcohol from the reaction mixture?

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Term used for base promoted hydrolysis

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Saponification

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Solvent

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The reflux temperature is near the boiling point of the _____.

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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.

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Azeotrope

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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.

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The ideal solvent for the recrystallization of a particular compound is one that:

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Top

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When two imiscible liquids are placed in a separatory funnel, the liquid with the lower density will form the __________ layer.

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A specific technique used to separate solid material from a solution.

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Vacuum Filtration

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Emulsion

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Instead of two distinct layers, sometimes a fog of particles forms in a separatory funnel and is known as an _______.

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It's the upper limit of the melting point range.

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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?

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is sharp, having a range of 1 degree or less.

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The melting point of a pure organic compound:

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Fraction

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Each component of a fractional distillation that is collected is known as a _______.

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Equilibrium

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All of the steps in the fractional distillation process are ___________ steps.

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Shorter

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A compound with a lower boiling point will have a _____________ retention time on a GC column than a compound with a higher boiling point.

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Boiling points

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The gas chromatography setup we will be using in this experiment (Dehydration of 2-Methylcyclohexanol) separates compounds based on their __________.

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Peaks, retention

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The printout you will receive from the GC is a plot of _________ vs. ________ time.

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Br2 in chloroform Test and KMnO4 Test

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Which of the following qualitative organic functional group tests will we be performing to test for the presence of C=C double bonds?

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1-methylcyclohexene

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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?

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Zaitsev's Rule

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What rule can we use before analyzing our GC plot to determine which of the possible alkene products should be the major product?

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Colorless

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The bromine solution is reddish-orange. Bromine reacts with an alkene to form a ------------ solution.

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Bottom

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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?

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Electron poor species

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Electrophile

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Electron rich species

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Nucleophile

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Sn2

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Primary Alcohols reacts via ______.

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Sn2 and Sn1

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Secondary Alcohols reacts via _______.

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Determines functional groups in a compound.

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IR

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Determines # and % of components in a sample.

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GC

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The structure of the reactants and the reaction conditions.

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Whether a reaction will proceed via an SN1 or an SN2 process depends on:

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Top

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When any of the alkylhalide products are mixed with 9M sulfuric acid in a separatory funnel, which layer will be the organic layer?

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To remove any unreacted alcohol from the distillate.

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Last week you carried out 4 extractions of your crude product. What was the purpose of the extraction with 9M H2SO4?

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A nucleophilic substitution reaction.

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The overall reaction of an alcohol with sodium bromide to produce an alkyl bromide and water is an example of:

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The major product is the more stable product with the more substituted double bond.

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Zaitsev's Rule

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A colorless solution with a brown MnO4 precipitate.

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The KMnO4 is purple. It reacts with an alkene to form:

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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.

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Synthesis of an alkyl halide lab:

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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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Dehydration of 2-Methylcyclohexan-1-ol lab:

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