Carboxylic Acids Nitriles Natural Products Nomenclature Acidity Preparation Reactions.
Chapter 16 Carbohydrates Classification Nomenclature Reactions.
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Transcript of Chapter 16 Carbohydrates Classification Nomenclature Reactions.
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Chapter 16
Carbohydrates
ClassificationNomenclature
Reactions
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Organic compounds in nature
• Carbohydrates are among the major classes of organic compounds found in nature.
• Others include: lipids, proteins and nucleic acids.
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Functions of Carbohydrates
Components of genetic material; DNA and RNA
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16.1Classification of Carbohydrates
• Many of this class of molecules have a common formula Cx(H2O)y which is carbon (carbo) and water (hydrate).
• Carbohydrate compounds are also known as sugars or saccharides.
• Carbohydrates are polyhydroxy aldehydes and ketones
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Classification of Carbohydrates
• Monosaccharide
• Oligosaccharide
• Polysaccharide
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Classification of Carbohydrates
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Monosaccharides
•Is not cleaved to a simpler carbohydrate on hydrolysis.
•Glucose (C6H12O6), for example, is a monosaccharide
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• Classification is based on:
1. Number of carbon atoms present
2. Whether the carbonyl group is an aldehyde or
ketone
Monosaccharides
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Trioses
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•No. of carbons Aldose Ketose• 4 Aldotetrose Ketotetrose• 5 Aldopentose Ketopentose• 6 Aldohexose Ketopentose• 7 Aldoheptose Ketoheptose• 8 Aldooctose Ketooctose
Some Classes of monosaccharides
•Aldoses: Monosaccharides that are polyhydroxy aldehydes
•Ketoses: Monosaccharides that are polyhydroxy ketones
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p. 462a
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16.3Chirality in Monosaccharides
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p. 462c
Fischer Projection
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p. 463a
D and L Notation
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p. 463b
D and L Notation
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• D-L is fundamentally different from R-S notation
• R-S is only used for single stereogenic center, while D-L is used for the whole molecule.
• Stereochemistry is assigned on basis of whetherconfiguration of highest-numbered stereogenic centeris analogous to D or L-glyceraldehyde.
D and L Notation
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p. 464, Fig. 16-1
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16.4
Cyclic Hemiacetal Structures of Monosaccharides
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Recall from Section 9.7
•Product is a hemiacetal.
R"OHC
•• O
••
R
R'
R"O CO H
••
••
••
••
R
R'
+
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Cyclic Hemiacetals
•Aldehydes and ketones that contain an OH group elsewhere in the molecule can undergo intramolecular hemiacetal formation.•The equilibrium favors the cyclic hemiacetal if the ring is 5- or 6-membered.
CO
R
OH
C
OHR
O
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p. 466, Fig. 16-2
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p. 467a
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p. 468
16.5Anomeric Carbons
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16.6Pyranose Structures
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16.6Furanose Structures
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p. 470a
16.6Furanose Structures
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Conformation of Pyranoses
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p. 470b
16.7Conformation of Pyranoses
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Reactions of Carbohydrates
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Carbohydrate Reactivity• Reactions of carbohydrates are similar to
other organic reactions already studied.• These reactions were once used extensively
for structure determination.• Reactions of carbohydrates can involve either
open-chain form, furanose, or pyranose forms.
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p. 471b
16.8Esters from monosaccharides
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p. 471b
16.8Ethers from monosaccharides
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p. 471b
16.9Reduction of monosaccharides
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p. 471b
16.10 Oxidation of monosaccharides
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p. 471b
16.10 Oxidation of monosaccharides
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p. 471b
16.10 Oxidation of monosaccharides
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Oxidation Occurs at the Ends• Easiest to oxidize the aldehyde and the
primary alcohol functions.
Aldonic acid Aldaric acid
CO2H
CH2OH
CO2H
CO2H
CH O
CH2OH
Aldose
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16.11Formation of glycosides from
monosaccharides
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16.11Formation of glycosides from
monosaccharides
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16.12Disaccharides
•Is cleaved to two monosaccharides on hydrolysis.–These two monosaccharides may be the same or different.
C12H22O11 + H2O
sucrose(a disaccharide)
C6H12O6 + C6H12O6
glucose(a monosaccharide) fructose
(a monosaccharide)
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Maltose
Maltose is composed of two glucose units linked together by a glycosidic bond between C-1 of one glucose and C-4 of the other.
Beer is made from four basic building blocks: water, malted barley, and hops.
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Cellobiose
Cellobiose is a stereoisomer of maltose. The only difference between the two is that cellobiose has a (1,4) glycosidic
bond while that of maltose is (1,4). Obtained from hydrolysis of cellulose
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Lactose(Milk Sugar)
Cellobiose and lactose are stereoisomeric disaccharides.Both have (1,4) glycosidic bonds.The glycosidic bond unites two glucose units in cellobiose. It unites galactose and glucose in lactose.
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Sucrose(Table sugar)
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16.13Polysaccharides
• Contain many linked monosaccharides• Vary in chain length and molecular weight• Most give a single monosaccharide on
complete hydrolysis• Monosaccharide units may be linearly
connected or may be branched
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Starch
• Starch- energy storing carbohydrate of plants– In cereals, rice, potatoes and corn
• Starch is a mixture of amylose and amylopectin, which are both composed of thousands of D-glucose units joined by α(1,4)-glycosidic linkages.
• Thus, they can be viewed as a repeating collection of maltose units
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Starch
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Starch
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Glycogen
• Glycogen- energy storing carbohydrate of animals
• More branched than starch(amylopectin)• Produced from glucose that is absorbed from
the intestines into the blood• Transported to the liver, muscles and then
polymerized enzymatically
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Cellulose
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Chitin
A tough, protective, semitransparent substance, primarily a nitrogen-containing polysaccharide, forming the principal component of arthropod exoskeletons and the cell walls of certain fungi.
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Pectin• structural heteropolysaccharide contained in the primary
cell walls of terrestrial plants. • It is produced commercially as a white to light brown
powder, mainly extracted from citrus fruits, and is used in food as a gelling agent particularly in jams and jellies.
• It is also used in fillings, medicines, sweets, as a stabilizer in fruit juices and milk drinks, and as a source of dietary fiber.