Game 7: Organic Chemistry/Carbohydrates
2nd semester, Vollhardt & Schore text, 3rd Ed.
Designed by a student group, Spring '02, JJG's Chem 0320.
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Carbohydrates
Single Jeopardy Answers
1. Potpourri
Pts Answer
50
An aldopentose has this number of stereoisomers.
100 These molecules differ in configuration at only
one carbon.
150 Two aldoses that form the same phenylosazone
differ in configuration at this chiral center.
Question
What is 8?
What are epimers?
What is C2; the chiral center
adjacent to the aldehyde?
200
Vigorous oxidation (using dilute HNO3 and heat)
of monosaccarides forms this product.
What is an aldaric acid?
250
Aldoses and ketoses mixed with three equivalents
of phenylhydrazine form these compounds.
What are osazones?
2. Polysacc
Pts Answer
50
Type of bond that holds two simple sugars
together.
100 Type of glycosidic linkage that occurs in cellulose
and starch.
150 Humans can’t use cellulose for food because they
don’t have the enzyme necessary to hydrolyze
this bond.
200 This molecule has been tried as a cancer treatment
and is also known as vitamin B17.
250 This is a nonsugar residue bonded to the anomeric
carbon of the acetal form of a sugar.
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Question
What is a glycosidic bond?
What is 1-4’?
What is the  link of cellulose?
What is Laetrile?
What is an aglycone?
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Carbohydrates
3. Reagents
Pts Answer
50
Question
OH
OCOCH(CH3)2
O
(H3C)2HCOCO
(H3C)2HCOCO
100
OH
??
O
HO
HO HO OH
150
OHO CH2OH
OH
??
OH
200
OHO CH2OH
What are:
((CH3)2CHCO)2O
and pyridine?
??
O
HO
HO OH
HO
OCOCH(CH3)2
OCOCH(CH3)2
COOH
H OH
HO H
H OH
H OH
COOH
CH2OH
HO H
HO H
H OH
CH2OH
H
HO
H
H
??
HO OH
HO
HO
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O
HO OH
??
H
H
H
What is:NaBH4?
What are:
1.)HCN
2.)H2,Pd/C
3.)HCl
4.)HNO3, heat
What are:
1.)NH2OH, CH3CO2Na,
(CH3CO)2O, XS pyridine
2.)H2O, H2SO4
3.)Br2, H2O
OR
1.)Br2/H2O
2.)Ca(OH)2
3.)Fe2(SO4)3
4.)30% H2O2
5.)Br2, H2O
COOH
OH
H
OH
OH
CH2OH
250
OH
What is:
HNO3 ?
COOH
OH
OH
OH
CH2OH
3
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Carbohydrates
4. Rxn ID
Pts
Answer
CHO
50
Question
What is cyclic
hemiacetal formation?
H
HO
H
H
100
150
200
250
OH
H3O
OH
H
H
O
O
2
OH
HO
HO
OH
OH OH
CH2OH
Fe2(SO4)3
H2O
CHO
CHO
heat
H OH
H OH
H OH
H OH
H2 O 2
H OH
CH2OH
CH2OH
Ag2O
CHO
COOH
H OH
H OH
NH4OH
HO H
HO H
H2O
H OH
H OH
CH2OH
CH2OH
OH
RCO2COR (xs)
O
HO
pyridine
HO
HO
OH
OCOR
O
ROCO
ROCO
ROCO OCOR
1. HCN
COOH
2. H2, Pd, BaSOH
OH
CHO
4
H OH
3. H3O+ / H2O H OH
H OH
H OH
H OH
H OH
CH2OH
CH2OH
5. Biochem
Pts Answer
50
Sugars, starches, and fibers are forms of this class
of molecules.
100 This reaction produces glucose to use as energy:
6CO2 + 6H2O  C6(H2O)6 + 6CO2.
150 The sea squirt is one of very few animals to use
this carbohydrate in its outer walls.
200 Glucose labeled with this serves as a radiotracer
to image the human brain.
250 This type of compound contains Rutinose and has
significant therapeutic value in maintaining
cardiovascular health.
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What is the Ruff
Degradation
Reaction?
What is the Tollens
Oxidation Reaction?
What is
Esterification?
What is KilianiFischer synthesis?
Question
What are carbohydrates?
What is photosynthesis?
What is cellulose?
What is 18F?
What are bioflavanoids?
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Carbohydrates
6. Naming
Pts Answer
CHO
50
H
H
H
H
100
150
200
250
Question
What is carbon 3?
OH
OH
OH
OH
CH2OH
A sugar with a five-member ring.
What are furanoses?
What is Glucose?
CHO
H
OH
HO
H
H
OH
H
OH
CH2OH
CHO
H
OH
CH2OH
H OH
HO
HO
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What is D-glyceraldehyde?
What is -D-Glucopyranose?
HO
H HO
H
HO
H
5
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