B.sc. III Chemistry Paper b. Submited by :- Dr. Sangeeta Mehtani Associate Professor Deptt. Of Chemistry PGGCG, sec11 Chd
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1 B.sc. III Chemistry Paper b Submited by :- Dr. Sangeeta Mehtani Associate Professor Deptt. Of Chemistry PGGCG, sec11 Chd
2 CARBOYDRATES
3 Carbohydrates polyhydroxyaldehydes or polyhydroxyketones of formula (C 2 O) n, or compounds that can be hydrolyzed to them. (aka sugars or saccharides) Carbohydrates are classified into following-: Monosaccharides carbohydrates that cannot be hydrolyzed to simpler carbohydrates; eg. Glucose or fructose. Disaccharides carbohydrates that can be hydrolyzed into two monosaccharide units; eg. Sucrose, which is hydrolyzed into glucose and fructose. Oligosaccharides carbohydrates that can be hydrolyzed into a few monosaccharide units. Polysaccharides carbohydrates that are are polymeric sugars; eg Starch or cellulose.
4 Aldoses (e.g., glucose) have an aldehyde group at one end. Ketoses (e.g., fructose) have a keto group, usually at C2. C O C 2 O C O O C C O C O C 2 O D-glucose C O O C C O C O C 2 O D-fructose Monosaccharides
5 Aldose polyhydroxyaldehyde, eg glucose Ketose polyhydroxyketone, eg fructose Triose, tetrose, pentose, hexose, etc. carbohydrates that contain three, four, five, six, etc. carbons per molecule (usually five or six); eg. Aldohexose, ketopentose, etc.
6 D vs L Designation D & L designations are based on the configuration about the single asymmetric C in glyceraldehyde. The lower representations are Fischer Projections. CO C O C 2 O D-glyceraldehyde CO C O C 2 O D-glyceraldehyde CO O C C 2 O L-glyceraldehyde CO O C C 2 O L-glyceraldehyde
7 Sugar Nomenclature For sugars with more than one chiral center, D or L refers to the asymmetric C farthest from the aldehyde or keto group. O O C C C O O C O C C O C O O C C O O C C 2 O C 2 O D-glucose L-glucose Most naturally occurring sugars are D isomers.
8 CO O O O O C 2 O (+)-glucose (+)-glucose? An aldohexose Emil Fischer (1902) Four chiral centers, 24 = 16 stereoisomers Exists only in solution. There are two solids: α-glucose m 146 o [α] = β-glucose m 150 o [α] = In water each mutarotates to an equilibrium with [α] = (63.6% β / 36.4% α)
9 Reducing sugar a carbohydrate that is oxidized by Tollen s, Fehling s or Benedict s solution. Tollen s: Ag + Ag (silver mirror) Fehling s or Benedict s: Cu 3+ (blue) Cu 2+ (red ppt) These are reactions of aldehydes and alpha-hydroxyketones. All monosaccharides (both aldoses and ketoses) and most * disaccharides are reducing sugars. * Sucrose (table sugar), a disaccharide, is not a reducing sugar.
10 Chemical Properties of D+ Glucose
11 Osazone Formation 1. 2.
12 Ruff degradation a series of reactions that removes the reducing carbon ( C=O ) from a sugar and decreases the number of chiral centers by one; used to relate configuration. CO O O C 2 O Br 2 2 O CO 2 O O C 2 O Ca 2+ CO O C 2 O D-(+)-glyceraldehyde 2 O 2 Fe 3 + CO 2 O O C 2 O
13 Kiliani-Fischer synthesis. A series of reactions that extends the carbon chain in a carbohydrate by one carbon and one chiral center. CO O C 2 O CN C N O O C 2 O O + C N O C 2 O +, 2 O COO O O O C 2 O COO O C 2 O CO O O C 2 O Na(g) O C 2 C O O O diastereomers separable - 2 O lactone
14 Epimers stereoisomers that differ only in configuration about one chiral center. CO CO O O O O O O O O C 2 O C 2 O D-glucose D-mannose epimers
15 Configuration of Glucose
16 aldotetroses * * C 2 CCC O O OO CO O O C 2 O O O CO C 2 O D-erythrose L-erythrose O CO O C 2 O O CO O C 2 O L-threose D-threose
17 RING STRUCTURE OF GLUCOSE
18 O O O O O O alpha-(+)-glucose O CO O O O C 2 O O O O O O beta-(+)-glucose O O C 2 O O O O O O C 2 O O O O O
19 GLYCOSIDES: Addition of alcohols to aldehydes/ketones: O R C O + R'O R C OR' hemiacetal geminal ether/alcohol reducing! OR' R C OR' acetal geminal diether non-reducing!
20 O O O O O O O CO O O O C 2 O O O O O O O nucleophilic addition of -O on carbon 5 to the aldehyde functional group O CO O O O C 2 O O O 2 C rotate C-5 O to rear C O O O O O O O O O O O O O O O O
21 O O O O O O O O O O O O alpha hemiacetal beta O D-glucopyranoses 4-Pyran
22 Thank you
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