Knewton’s Review of Functional Groups and Carbohydrates
Knewton’s Content Team Review of Functional GroupsKnewton’s Content Team Review of Functional Groups
Page 1: Types of Carbohydrates
Differentiate between types of carbohydrates
Table: Part 1
Page 2: Types of Carbohydrates
Differentiate between types of carbohydrates
Table: Part 2
Page 3: Cyclic Compounds
Cyclic Organic Compounds: Organic compounds can be cyclic (rings). They are named based on the number of carbons in the ring, with "cyclic" prefacing the name.
Cyclic Alkanes: Examples include:
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Page 4: Cyclic Alkanes Continued
Examples of cyclic alkanes:
Methylcyclopentane
Methylcyclohexane
1,2-dimethylcyclohexane
1,3-dimethylcyclohexane
cis-1,2-dimethylcyclohexane
trans-1,2-dimethylcyclohexane
Page 5: Cyclic Alkenes
Cyclic Alkenes: Examples include:
Cyclopentene
Cyclohexene
1-Methylcyclohexene
1,2-dimethylcyclohexene
1,6-dimethylcyclohexene
Page 6: Cyclic Alcohols
Cyclic Alcohols: Examples include:
Cyclopropanol
Cyclobutanol
Cyclopentanol
cis-2-methylcyclohexanol
Cyclohexanol
2-Methylcyclohexanol
trans-4-methylcyclohexanol
Page 7: Cyclic Ketones
Cyclic Ketones: Examples include:
Cyclopentanone
Cyclohexanone
2-Methylcyclopentanone
2-Methylcyclohexanone
4-Methylcyclohexanone
Page 9: Overview of Carbohydrates
Carbohydrate Structures and Classifications
Carbohydrates: Macromolecules made of sugars.
The name carbohydrate derives from carbon (carbo-) and water (-hydrate).
Simple carbohydrates are defined by the formula:
where ( n ) is the number of carbon atoms.Complex carbohydrates maintain a structure close to this formula.
Page 11: Subtypes of Carbohydrates
Carbohydrates are classified into three subtypes based on the number of simple sugar units:
Monosaccharides: Single sugar units.
Disaccharides: Two monosaccharides.
Polysaccharides: Long chains of monosaccharides.
Page 13: Monosaccharides
Monosaccharides are simple sugars, examples include:
Glucose (C6H12O6): The most common monosaccharide, an important source of energy.
Fructose
Galactose
Mannose
Ribose
Names of monosaccharides generally end with the suffix -ose.
Page 14: Sugar Classification by Functional Groups
Aldoses: Sugars with an aldehyde group (R-CHO).
Ketoses: Sugars with a ketone group (R-C(O)-R’).
Page 15: Sugar Classification by Carbon Number
Sugars are classified according to the number of carbons in their structure.
Page 16: Cyclic Forms of Monosaccharides
Monosaccharides like glucose can form rings (cyclic compounds).
Page 17: Disaccharides Formation
Disaccharides form when two monosaccharides undergo a condensation reaction, creating a glycosidic linkage. They can be hydrolyzed by acid or enzymes. Common examples include:
Lactose: Galactose & Glucose
Sucrose: Glucose & Fructose
Maltose: Glucose & Glucose
Page 19: Polysaccharides
Polysaccharides are long chains of monosaccharides joined by glycosidic linkages. They can be branched or unbranched and can consist of different types of monosaccharides.
Functions include energy storage and providing structural support.
Common examples: Starch, glycogen, cellulose, chitin.
Page 20: Understanding Ketohexose
Question: How many carbons and what kind of functional groups are present in a ketohexose?
Solution: A ketohexose is a sugar (indicated by “-ose”) containing six carbons (hex-) and a ketone carbonyl group (keto-). It possesses hydroxyl groups attached to all non-carbonyl carbons.
Page 21: Biological Importance of Glucose vs. Glycogen
Question: How do the biological importance of glucose and glycogen differ?
Solution: Glucose molecules are broken down to create energy, whereas glycogen serves as an energy storage form in the body.
Page 23: Introduction to Chirality
Chirality: Chirality is defined as a property whereby an object is asymmetrical, preventing it from being superimposed on its mirror image.
Chiral: Objects that are not superimposable on their mirror images.
Achiral: Objects that can be superimposed on their mirror images.
Page 26: Chiral Carbon Atoms
Molecular Geometry: Determines whether a molecule is chiral or achiral. A chiral carbon is a carbon atom attached to four different atoms or groups, referred to as a chiral center.
Page 28: General Rules for Chirality
If a molecule contains one chiral carbon, then it is chiral.
If it contains two or more chiral carbons, the molecule may be either chiral or achiral.
Page 29: Enantiomers
Enantiomers: Stereoisomers with the same bond structure but different arrangement in space. They possess similar chemical and physical properties with the exception of interactions with chiral molecules.
Page 32: Fischer Projections
Fischer Projections: A method for representing the 3D arrangement of atoms in enantiomers or stereoisomers. Commonly used for monosaccharides.
They depict multiple chiral carbons efficiently and are analogous to expanded structural formulas.
Page 34: Drawing Fischer Projections
Rules for Drawing Fischer Projections:
The main carbon chain is vertical, with bonds assumed to bend into the plane of the structure.
The most oxidized carbon is positioned near the top.
Other atoms/groups are added with horizontal bonds assumed to come out of the plane.
Page 36: Identifying D and L Sugars
Determine the last chiral carbon in the chain:
If the hydroxyl group (-OH) is on the right, it designates a D sugar.
If it is on the left, it designates an L sugar.
Page 40: Haworth Structures
Conversion to Haworth Projections: Monosaccharides exist in equilibrium between linear and cyclic forms, with a preference for cyclic forms. Each form preserves the molecular identity.
Page 41: Glycosidic Linkages
Glycosidic Linkages: Formed between two ringed sugars by an ether group. At least one side connects to an anomeric carbon (the carbon in a sugar ring that is linked to two oxygen atoms due to the carbonyl carbon in the linear form).
Page 62: Polysaccharide Structure and Function
Polysaccharides as long chains:
Storage Polysaccharides: Used to store energy.
Structural Polysaccharides: Provide rigidity, are harder to digest by predators.
Page 67: Cellulose
Cellulose: A structural polysaccharide giving rigidity to plant cell walls. It features β 1-4 linkages between glucose monomers, creating a tightly packed structure.
Some animals possess enzymes (cellulase) to aid in digestion.
Page 70: Metabolism of Glycogen vs. Cellulose
Question: Why can humans metabolize glycogen but not cellulose?
Solution: Glycogen consists of alpha linkages between glucose molecules, which are hydrolyzed by human enzymes, whereas cellulose has beta linkages that humans lack the necessary enzymes to break down.
Page 1: Types of Carbohydrates - Differentiate between types of carbohydrates - Table: Part 1
Page 2: Types of Carbohydrates - Differentiate between types of carbohydrates - Table: Part 2
Page 3: Cyclic Compounds - Cyclic Organic Compounds: Organic compounds can be cyclic (rings). They are named based on the number of carbons in the ring, with "cyclic" prefacing the name. - Cyclic Alkanes: Examples include:
Cyclopropane
Cyclobutane
Cyclopentane
Cyclohexane
Page 4: Cyclic Alkanes Continued - Examples of cyclic alkanes:
Methylcyclopentane
Methylcyclohexane
1,2-dimethylcyclohexane
1,3-dimethylcyclohexane
cis-1,2-dimethylcyclohexane
trans-1,2-dimethylcyclohexane
Page 5: Cyclic Alkenes - Cyclic Alkenes: Examples include:
Cyclopentene
Cyclohexene
1-Methylcyclohexene
1,2-dimethylcyclohexene
1,6-dimethylcyclohexene
Page 6: Cyclic Alcohols - Cyclic Alcohols: Examples include:
Cyclopropanol
Cyclobutanol
Cyclopentanol
cis-2-methylcyclohexanol
Cyclohexanol
2-Methylcyclohexanol
trans-4-methylcyclohexanol
Page 7: Cyclic Ketones - Cyclic Ketones: Examples include:
Cyclopentanone
Cyclohexanone
2-Methylcyclopentanone
2-Methylcyclohexanone
4-Methylcyclohexanone
Page 9: Overview of Carbohydrates - Carbohydrate Structures and Classifications - Carbohydrates: Macromolecules made of sugars. - The name carbohydrate derives from carbon (carbo-) and water (-hydrate). - Simple carbohydrates are defined by the formula:
where ( n ) is the number of carbon atoms. - Complex carbohydrates maintain a structure close to this formula.
Page 11: Subtypes of Carbohydrates - Carbohydrates are classified into three subtypes based on the number of simple sugar units:
Monosaccharides: Single sugar units.
Disaccharides: Two monosaccharides.
Polysaccharides: Long chains of monosaccharides.
Page 13: Monosaccharides - Monosaccharides are simple sugars, examples include:
Glucose (C6H12O6): The most common monosaccharide, an important source of energy.
Fructose
Galactose
Mannose
Ribose
Names of monosaccharides generally end with the suffix -ose.
Page 14: Sugar Classification by Functional Groups - Aldoses: Sugars with an aldehyde group (R-CHO).
Ketoses: Sugars with a ketone group (R-C(O)-R’).
Page 15: Sugar Classification by Carbon Number - Sugars are classified according to the number of carbons in their structure.
Page 16: Cyclic Forms of Monosaccharides - Monosaccharides like glucose can form rings (cyclic compounds).
Page 17: Disaccharides Formation - Disaccharides form when two monosaccharides undergo a condensation reaction, creating a glycosidic linkage. They can be hydrolyzed by acid or enzymes. Common examples include:
Lactose: Galactose & Glucose
Sucrose: Glucose & Fructose
Maltose: Glucose & Glucose
Page 19: Polysaccharides - Polysaccharides are long chains of monosaccharides joined by glycosidic linkages. They can be branched or unbranched and consist of different types of monosaccharides. - Functions include energy storage and providing structural support. - Common examples: Starch, glycogen, cellulose, chitin.
Page 20: Understanding Ketohexose - Question: How many carbons and what kind of functional groups are present in a ketohexose? - Solution: A ketohexose is a sugar (indicated by “-ose”) containing six carbons (hex-) and a ketone carbonyl group (keto-). It possesses hydroxyl groups attached to all non-carbonyl carbons.
Page 21: Biological Importance of Glucose vs. Glycogen - Question: How do the biological importance of glucose and glycogen differ? - Solution: Glucose molecules are broken down to create energy, whereas glycogen serves as an energy storage form in the body.
Page 23: Introduction to Chirality - Chirality: Chirality is defined as a property whereby an object is asymmetrical, preventing it from being superimposed on its mirror image. - Chiral: Objects that are not superimposable on their mirror images. - Achiral: Objects that can be superimposed on their mirror images.
Page 26: Chiral Carbon Atoms - Molecular Geometry: Determines whether a molecule is chiral or achiral. A chiral carbon is a carbon atom attached to four different atoms or groups, referred to as a chiral center.
Page 28: General Rules for Chirality - If a molecule contains one chiral carbon, then it is chiral. - If it contains two or more chiral carbons, the molecule may be either chiral or achiral.
Page 29: Enantiomers - Enantiomers: Stereoisomers with the same bond structure but different arrangement in space. They possess similar chemical and physical properties with the exception of interactions with chiral molecules.
Page 32: Fischer Projections - Fischer Projections: A method for representing the 3D arrangement of atoms in enantiomers or stereoisomers. Commonly used for monosaccharides. - They depict multiple chiral carbons efficiently and are analogous to expanded structural formulas.
Page 34: Drawing Fischer Projections - Rules for Drawing Fischer Projections:
The main carbon chain is vertical, with bonds assumed to bend into the plane of the structure.
The most oxidized carbon is positioned near the top.
Other atoms/groups are added with horizontal bonds assumed to come out of the plane.
Page 36: Identifying D and L Sugars - Determine the last chiral carbon in the chain:
If the hydroxyl group (-OH) is on the right, it designates a D sugar.
If it is on the left, it designates an L sugar.
Page 40: Haworth Structures - Conversion to Haworth Projections: Monosaccharides exist in equilibrium between linear and cyclic forms, with a preference for cyclic forms. Each form preserves the molecular identity.
Page 41: Glycosidic Linkages - Glycosidic Linkages: Formed between two ringed sugars by an ether group. At least one side connects to an anomeric carbon (the carbon in a sugar ring that is linked to two oxygen atoms due to the carbonyl carbon in the linear form).
Page 62: Polysaccharide Structure and Function - Polysaccharides as long chains:
Storage Polysaccharides: Used to store energy.
Structural Polysaccharides: Provide rigidity, are harder to digest by predators.
Page 67: Cellulose - Cellulose: A structural polysaccharide giving rigidity to plant cell walls. It features β 1-4 linkages between glucose monomers, creating a tightly packed structure. - Some animals possess enzymes (cellulase) to aid in digestion.
Page 70: Metabolism of Glycogen vs. Cellulose - Question: Why can humans metabolize glycogen but not cellulose? - Solution: Glycogen consists of alpha linkages between glucose molecules, which are hydrolyzed by human enzymes, whereas cellulose has beta linkages that humans lack the necessary enzymes to break down.
Carbohydrates
Definition: Macromolecules made of sugars, derived from carbon (carbo-) and water (-hydrate).
Key Points:
Simple carbohydrates are defined by the formula (CH₂O)ₙ, where (n) is the number of carbon atoms.
Complex carbohydrates maintain a structure close to this formula.
Examples:
Glucose
Fructose
Galactose
Subtypes of Carbohydrates
Definition: Classifications of carbohydrates based on simple sugar units.
Key Points:
Monosaccharides: Single sugar units.
Disaccharides: Two monosaccharides.
Polysaccharides: Long chains of monosaccharides.
Examples:
Monosaccharides: Glucose, Fructose
Disaccharides: Lactose (Galactose + Glucose), Sucrose (Glucose + Fructose)
Polysaccharides: Starch, Glycogen
Biological Importance
Definition: Differences in function between glucose and glycogen.
Key Points:
Glucose: Broken down to create energy.
Glycogen: Serves as an energy storage form in the body.
Examples:
Glucose is used as a primary energy source in cells.
Glycogen is stored in liver and muscle cells.
Chirality
Definition: Property of an object being asymmetrical and unable to be superimposed on its mirror image.
Key Points:
Chiral: Not superimposable on its mirror image.
Achiral: Can be superimposed on its mirror image.
Examples:
Chiral molecule: Lactic acid
Achiral molecule: Carbon dioxide
Enantiomers
Definition: Stereoisomers with the same bond structure but different spatial arrangements.
Key Points:
They share similar chemical and physical properties except in interactions with chiral molecules.
Examples:
L-dopa and D-dopa (which are used in treating Parkinson's disease)
Fischer Projections
Definition: A method of representing the 3D arrangement of atoms in enantiomers or stereoisomers.
Key Points:
Main carbon chain is vertical; the most oxidized carbon is near the top.
Examples:
Commonly used to depict sugar molecules.
Haworth Structures
Definition: Cyclic forms of monosaccharides showing equilibrium with linear forms.
Key Points:
Preference for cyclic forms in monosaccharides.
Examples:
Glucose can exist as both linear and cyclic forms, with the cyclic version being more predominant.