ACS Organic Chemistry Exam Practice
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Test with correct solutions. __., __., __., __.,
What is an elimination reaction?
__., When the leaving group and a
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proton on an adjacent carbon both leave to form a double bond
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What is the term for the most basic type of eliminations?
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eliminations (because proton and leaving group are on adjacent atoms);
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this can also be called beta-elimination
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Distinguish between alpha and beta anomers. __.,beta anomers have the __., __., __., __., __.,__., __., __., __., __.,
OH belonging to the hemiacetal carbon equatorial
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alpha anomers have the OH belonging to the hemiacetal carbon axial
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What is the definition of mutarotation?
__., __., the process for which alpha
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and beta anomers come to equilibrium (aqueous) in a specific ratio. It is
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the same ratio is observed when you start with the alpha anomer in
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water versus the beta anomer in water
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What is the general formula for a carbohydrate?
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How do you determine the number of stereoisomers for a given
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carbohydrate?
, 2^n where n= number of stereocenters __.,__., __., __., __., __., __., __.,
Distinguish between the D and L designations for carbohydrates.
__., In __., __., __., __., __., __., __., __.,__., __., __.,
the L form the hydroxy group is on the bottom left closest to the CH2O
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H group in the frame of a Fischer projection
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, In the D form the OH is on the bottom right
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What are anomers? Diastereomers formed by the cyclization of
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carbohydrates (*note they have different configurations at the new
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stereocenter-this is what makes them diastereomers) __., __., __., __., __.,
What agent is most often used for complete oxidation of a carbohydrate?
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HNO3
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What kind of agents are used for selective or partial oxidation of carbohy
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drates? most commonly Br or some other MILD oxidative agent
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What are reducing sugars?
__., Carbohydrates that yield positive results
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of the oxidative tests, because in being oxidized they reduce the metal
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ion (or other reducing agent)
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Carbohydrates undergo reactions similar to which functional group?
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OH (hemiacetals and acetals)
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How does the Tollen's test work?
__., Carbohydrate is oxidized by Ag+
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and positive result shows a silvery mirror as Ag+ is reduced to metallic
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(elemental) silver __.,
How do the Benedict's and Fehling's tests work?
__., __., Both employ a
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solution of aqueous Cu2+ in base. When reduced it forms Cu2O which is
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a red ppt.
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