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1. Announcements & Agenda (04/09/07) Extra Credit Assignment Due NOW! Pick Up ... found in fruits, corn syrup, and honey. an aldohexose with the formula C6H12O6 ...
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Title: Announcements 1 Announcements Agenda (04/09/07)
  • Extra Credit Assignment Due NOW!
  • Pick Up Graded Quizzes
  • Quiz Friday (13.4, 13.5, Ch 14)
  • Today
  • More on Carbohydrates (14.1-14.3)
  • Monosaccharides
  • Cyclic Monosaccharides
  • Reactions of carbohydrates
  • Disaccharides
  • 2 Last Time Amide Hydrolysis
  • acid hydrolysis
  • O
  • O CH3COH NH4Cl
  • HCl H2O
  • CH3CNH2
  • NaOH O
  • CH3CO Na NH3
  • base hydrolysis
  • 3 Last Time Carbohydrates Intro
  • a major source of energy from our diet
  • composed of C, H, O
  • also known as saccharides, which means sugars.
  • 4 Last Time Types of Carbohydrates
  • Monosaccharides simplest carbohydrates.
  • Disaccharides consist of two monosaccharides.
  • Polysaccharides contain many monosaccharides.
  • 5 Last Time Monosaccharides
  • typically 3-6 carbon atoms
  • have a CO group (aldehyde or ketone)
  • aldoses
  • ketoses
  • several hydroxyl groups
  • 6 Aldoses O C-H aldose H- C-OH H- C-OH CH2OH Erythose
  • monosaccharides with an aldehyde group
  • and many hydroxyl groups.
  • triose (3C atoms)
  • tetrose (4C atoms)
  • pentose (5C atoms)
  • hexose (6C atoms)
  • 7 Ketoses CH2OH CO ketose H- C-OH H- C-OH H-C-OH CH2OH
  • monosaccharides with a ketone group
  • and many hydroxyl groups.
  • Fructose, a ketohexose 8 Fischer Projections
  • also used to represent carbohydrates.
  • places the most oxidized group at the top.
  • shows chiral carbons as the intersection of vertical and horizontal lines.
  • 9 D L Notations Know This Now
  • In a Fischer projection, the -OH group on the
  • chiral carbon farthest from the carbonyl group determines an L or D isomer.
  • left L for the L-form.
  • right D for the D-form. (MOST COMMON IN NATURE!)
  • 10 Learning Check
  • Identify each as the D or L isomer.
  • A. B. C.
  • __-Ribose __- Threose __- Fructose
  • L D L 11 D-Glucose
  • found in fruits, corn syrup, and honey
  • an aldohexose with the formula C6H12O6
  • known as blood sugar in the body
  • the monosaccharide in polymers of starch, cellulose, and glycogen
  • 12 Blood Glucose Level
  • In the body,
  • normal blood glucose 70-90 mg/dL.
  • a glucose tolerance test measures blood glucose for several hours after ingesting glucose.
  • 13 D-Fructose
  • is a ketohexose C6H12O6
  • is the sweetest carbohydrate
  • found in fruit juices and honey
  • converts to glucose in the body
  • 14 D-Galactose
  • is an aldohexose C6H12O6.
  • not found free in nature.
  • is obtained from lactose, a disaccharide.
  • has a similar structure to glucose except for the
  • OH on C4
  • Which C is C4???
  • 15 Cyclic Structures (14.3)
  • prevalent form of monosaccharides with 5 or 6 carbon atoms
  • form when the hydroxyl group on C-5 reacts with the aldehyde group or ketone group
  • Orgo-Chem reaction not previously mentioned CO ROH ? hemiacetal
  • 16 Drawing Cyclic Structures Practice! Example Glucose
  • STEP 1 Number the carbon chain and turn clockwise to form a linear open chain.
  • 1 2 3 4 5 6 6 5 4 3 2 1 17 Cyclic Structure for Glucose
  • STEP 2 Fold into a hexagon.
  • Bond the C5 O to C1.
  • Place the C6 group above the ring.
  • Write the OH groups on C2 C4 below the ring (These are the C atoms that pointed down from Step 1).
  • Write the OH group on C3 above the ring.
  • Write a new OH on C1.
  • 6 5 4 1 3 2 18 Cyclic Structure for Glucose
  • STEP 3 Write the new OH on C1
  • down for the ? form.
  • up for the ? form.
  • ? ? ?-D-Glucose ?-D-Glucose 19 Summary of the Formation of Cyclic Glucose 20 Mutarotation
  • cyclic structures open and close.
  • ?-D-glucose converts to ß-D-glucose vice versa.
  • at any time, only a small amount of open chain forms.
  • ?-D-glucose D-glucose (open) ß-D-glucose
  • (36) (trace) (64)
  • 21 Cyclic Structure of Fructose
  • is a ketohexose.
  • reacts the -OH on C-5 with the CO on C-2
  • a-D-fructose D-fructose ?-D-fructose 22
  • Chemical Properties of
  • Monosaccharides (14.4)
  • 23 Reducing Sugars
  • are monosaccharides that oxidize to give a carboxylic acid.
  • undergo reaction in the Benedicts test.
  • include the monosaccharides glucose, galactose, and fructose.
  • 24 Oxidation of D-Glucose O QUESTION WHY CAN FRUCTOSE (A KETONE) BE OXIDIZED??? ANSWER ISOMERIZATION TO AN ALDEHYDE 25 One Test for Glucose in Urine Benedicts Test 26 Reduction of Monosaccharides D-Glucitol
  • involves the carbonyl group.
  • produces sugar alcohols, or alditols.
  • such as D-glucose gives D-glucitol also called sorbitol.
  • 27 Learning Check
  • Write the products of the oxidation and reduction of D-mannose.
  • D-mannose 28 Solution D-mannitol D-mannose D-mannonic acid 29 Disaccharides (14.5) 30 Important Disaccharides Know These 3
  • A disaccharide consists of two monosaccharides.
  • Monosaccharides Disaccharide
  • glucose glucose maltose H2O
  • glucose galactose lactose H2O
  • glucose fructose sucrose H2O
  • 31 Maltose
  • A.K.A. malt sugar
  • obtained from starch hydrolysis
  • used in cereals, candies, and brewing
  • linked by an ?-1,4-glycosidic bond formed from the ? -OH on C1 of the 1st glucose and -OH on C4 of the 2nd glucose
  • found in both the ?- and ß - forms
  • Free a-OH 32 Lactose
  • a disaccharide of ß-D-galactose and a- or ß-D-glucose.
  • contains a ß -1,4-glycosidic bond.
  • is found in milk and milk products.
  • a-form a-form 33 Sucrose
  • Sucrose or table sugar
  • is obtained from sugar cane and sugar beets.
  • consists of a-D-glucose and ß-D-fructose..
  • has an a,ß-1,2-glycosidic bond.
  • a-D-glucose ß -D-fructose 34 Learning Check
  • Write the structures of the two monosaccharides that form when sucrose is hydrolyzed.
  • 35 Solution
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