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Galactose, a monosaccharide component of lactose found in milk, exists predominantly in its cyclic form rather than its open-chain form. Would an aqueous solution of galactose give a positive Fehling's test? Justify your answer.
Which of the OH groups in β-D-altropyranose are in the axial position?
D-mannose is a monosaccharide that can exist in either pyranose and/or furanose forms. Draw the plausible Haworth projection of β-D-mannofuranose.
Determine the equilibrium percentages of α-D-fructose and β-D-fructose using their specific rotations. The specific rotation of α-D-fructose is +92°, that of β-D-fructose is +18°, and the equilibrium mixture has a specific rotation of +38.5°.
Use the given figures to determine the C-3 epimer of D-altrose.
Provide a mechanism for the acid-catalyzed reaction shown below and identify the type of reaction.
After methylated D-sorbofuranose is hydrolyzed, what do the results imply about the relationship between D-sorbofuranose and D-sorbose?
Predict the product obtained in the following reaction.
Some protecting groups can protect two hydroxy groups on a carbohydrate at the same time. One such group protects the OH groups at carbon 4 and carbon 6 of β-D-mannose, as shown below.
a. To what functional group does this protecting group belong?
b. What reagent is employed in the synthesis of such protected compounds?
c. When this blocking group is coupled with β-D-mannose, a new chiral center is formed. What is its location?
d. Draw the compound's other stereoisomer and assess which stereoisomer should be more stable.
Consider the following reaction of β-D-galactose with isopropylamine and explain why only a small amount of acid is used for the formation of an N-glycoside.
Determine the product of the reaction of D-ribose with Tollens’ reagent (Ag+, NH3, OH−).
When a modified Kiliani-Fischer synthesis begins with L-lyxose, what monosaccharides are produced?
An optically inactive alditol forms when aldose X undergoes reduction with sodium borohydride. When X undergoes Wohl degradation, Y is formed which converts to an optically active alditol. When Y undergoes Wohl degradation, D-threose is formed. Determine the identity of X and Y.
Ruff degradation of D-mannose produces D-arabinose. Ruff degradation of D-arabinose produces D-erythrose. What are the Fischer structures of D-arabinose and D-erythrose?
Provide the reaction equation that represents how Tollen's reagent gets reduced by the α-anomer lactose.
Between chitin and chitosan, determine the main structural differences.
Show how to prepare any of the standard amino acids from the compound shown below. You can use any reagents you need to accomplish the synthesis.
Show how D-leucine can be synthesized from the L-enantiomer of leucic acid
Draw the three-dimensional form of L-asparagine.
What are the predominant structures of valine, arginine, and glutamic acid in a solution with pH = 3?
i. Aspartic acid has an isoelectric point at pH 2.8. Draw its most prominent forms at pH levels 1, 2.8, 5, and 11.
ii. Explain why the carboxylic side chain of aspartic acid is less acidic than its carboxylic acid near the α-carbon atom.