Announcements

1
Announcements Agenda (04/04/07)

• Will start with quiz today
• Review session today _at_ 3pm (same place)
• Today
• Amides (13.5)
• Sugars! Section 14.1-14.3
• Carbohydrates
• Monosaccharides
• Cyclic Monosaccharides (?)

2
Last Time Hydrolysis of Esters

• an ester reacts with water to produce a
  carboxylic acid and an alcohol.
• an acid catalyst is required.
• O
• ??
  H
• HCOCH2CH3 H2O
• O
• ??
• HCOH HOCH2CH3

Base Hydroylsis forms an alcohol plus the salt of
a carboxylic acid!
3
What acid and alcohol make the following ester?

0

• Ethanol (2C) and acetic acid (2C)
• Propanol (3C) acetic acid (2C)
• Ethanol (2C) propionic acid (3C)
• Methanol (1C) propionic acid (3C)

4
Last Time Base Hydrolysis of Triglycerides Make
Soaps
5
Last Time Amines (Derivatives of NH3)

• Typically 3 kinds
• primary (1) amines 1 carbon group is bonded to
  N
• secondary (2) amines 2 carbon groups bonded to
  N
• tertiary (3) amines 3 carbon groups bonded to
  N.
• Can H-bond like alcohols, although N is not as
  polar
• decent BPs solubility in water
• Act as weak bases

CH3NH2 H2O CH3NH3 OH

• Useful properties of amine salts
• solids at RT, very soluble in body fluids
  (ideal for drug molecules, and salts dont stink ?

6
Last Time Alkaloids

• physiologically active nitrogen-containing
  compounds.
• often addictive.

nicotine
7
Morphine and Codeine

• alkaloids.
• obtained from the oriental poppy plant.
• used as painkillers.
• modified to make heroin.

8
Chocolate

• Chocolate is found in cocoa beans

9
Last Time Amides (13.5) made from Amine
Carboxylic Acid

• Amides are produced
• by reacting a carboxylic acid with ammonia
• or an amine (1 or 2).
• using heat.
• O O
• ?? Heat ??
• CH3COH NH3 CH3CNH2 H2O
• O O
• ?? Heat ??
• CH3COH CH3NH2 CH3CNHCH3 H2O

10
Some Amides in Health and Medicine

11
Physical Properties of Amides

• SIMILAR TO AMINES
• primary (-NH2) or secondary (-NH-) amides form
  hydrogen bonds.
• primary have higher mps than secondary.
• tertiary (no H on N) do not form hydrogen bonds
  have lower melting points.
• all form hydrogen bonds with water.
• with 1-5 carbon atoms are soluble in water.

12
Hydrolysis of AmidesIMPORTANT TO KNOW

• Amides undergo
• Acid hydrolysis to produce a carboxylic acid and
  an ammonium salt.
• Base hydrolysis to produce the salt of a
  carboxylic acid and an amine or ammonia.
• REACTIONS LOOK SIMILAR TO THOSE OF
  ESTERS!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
  !!

13
Hydrolysis Reactions

• acid hydrolysis
• 
  O
• O CH3COH
  NH4Cl
• HCl H2O
• CH3CNH2
• NaOH O
• CH3CO Na NH3
• base hydrolysis

14
Ch 14 Carbohydrates

• a major source of energy from our diet
• composed of C, H, O
• also known as saccharides, which means sugars.

15
Practice Problems (Ch 14)
14.05, 14.07, 14.09, 14.13, 14.15, 14.19, 14.21,
14.23, 14.25, 14.27, 14.29, 14.31, 14.33, 14.35,
14.37, 14.39, 14.41, 14.47, 14.49,
14.51, 14.53, 14.57, 14.59
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Carbohydrates

• produced by photosynthesis in plants
• Example glucose synthesized in plants from CO2,
  H2O, and energy from the sun.
• are oxidized in living cells to produce CO2, H2O,
  and energy.

17
Types of Carbohydrates

• Monosaccharides simplest carbohydrates.
• Disaccharides consist of two monosaccharides.
• Polysaccharides contain many monosaccharides.

18
Monosaccharides

• typically 3-6 carbon atoms
• have a CO group (aldehyde or ketone)
• aldoses
• ketoses
• several hydroxyl groups

19
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)

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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
21
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.

22
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!)

23
Learning Check

• Identify each as the D or L isomer.
• A. B. C.
• __-Ribose __- Threose __-
  Fructose

L
D
L
24
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

25
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.

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D-Fructose

• is a ketohexose C6H12O6
• is the sweetest carbohydrate
• found in fruit juices and honey
• converts to glucose in the body

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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???

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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

29
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
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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
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Cyclic Structure for Glucose

• STEP 3 Write the new OH on C1
• down for the ? form.
• up for the ? form.

?
?
?-D-Glucose ?-D-Glucose
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Summary of the Formation of Cyclic Glucose
33
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)

34
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