Organic Molecules and Functional Groups

Definition of Organic

  • For a compound to be considered organic in chemistry, it must contain both carbon and hydrogen.

  • This differs from the term "organic" used in grocery stores, which typically refers to pesticide-free produce.

Carbon's Versatility and Bonding

  • Valence Electrons: Carbon needs 44 valence electrons to be "happy" (to achieve a maximum of 88 electrons in its outer shell).

  • Bonding Needs: This means carbon needs to form 44 additional bonds to achieve stability.

  • Covalent Sharing: The most common way carbon forms these bonds is through covalent sharing with other atoms.

  • Structural Backbone: Carbon's ability to form 44 bonds makes it highly versatile, allowing it to create various "backbones" and "scaffolding" for all necessary organic molecules.

  • Types of Bonds: Carbon can form:

    • Single bonds: Shares one pair of electrons (represented by a single line).

    • Double bonds: Shares two pairs of electrons (represented by a double line).

    • Triple bonds: Shares three pairs of electrons (represented by a triple line).

    • No quadruple bonds are typically formed by carbon.

  • Four Bonds Rule: Every carbon atom in a stable organic molecule must have exactly 44 bonds. This can be checked visually in structures.

    • For example, in a CH3CH_3 group, the carbon forms 33 bonds with hydrogen and 11 bond with another atom.

Hydrogen's Bonding

  • Valence Electrons: Hydrogen has 11 valence electron.

  • Bonding Needs: It is happiest with 22 electrons, so it needs to form 11 more bond.

  • Hydrogen can either give away its electron or, more commonly with nonmetals, share it covalently.

  • Often, the single bond for hydrogen is understood and not explicitly drawn with a line connecting it to its parent atom.

Hydrocarbons

  • Definition: Compounds composed only of carbon and hydrogen.

  • Examples: These can exist as long chains, branched chains, or rings.

  • Properties: Hydrocarbons are characteristically nonpolar and hydrophobic (do not like water).

  • Relevance: This property is a key feature in lipids, explaining why oil and water do not mix.

  • Length: Hydrocarbon chains can vary significantly in length, from just two carbons to 5050 or more.

SPONCH Elements and Valence Needs

  • The most common elements that attach to carbon and hydrogen in organic molecules form the acronym SPONCH: Sulfur, Phosphorus, Oxygen, Nitrogen, Carbon, and Hydrogen.

  • These elements typically bond covalently by sharing electrons because they are nonmetals.

  • Valence Electron Requirements:

    • Hydrogen (H): Has 11 valence electron and needs 11 more bond to be happy.

    • Oxygen (O): Has 66 valence electrons and needs 22 more bonds to be happy.

    • Nitrogen (N): Has 55 valence electrons and needs 33 more bonds to be happy.

    • Carbon (C): Has 44 valence electrons and needs 44 more bonds to be happy.

Isomers

  • Definition: Isomers are compounds that have the same chemical formula but a different arrangement of atoms (different structure).

  • Example: Glucose, Fructose, and Galactose.

    • All three have the chemical formula C<em>6H</em>12O6C<em>6H</em>{12}O_6.

    • Despite having the same number of carbons, hydrogens, and oxygens, their structural arrangements differ.

    • Fructose forms a pentagonal ring, while glucose and galactose form hexagonal rings.

    • Glucose and galactose primarily differ by the orientation (flipped positions) of certain OH-OH (hydroxyl) groups.

  • Significance: While they are all sugars and serve similar basic functions, their differing arrangements can lead to distinct biological properties.

Functional Groups

  • Definition: Specific groups of atoms attached to carbon chains that impart particular chemical properties and functions to the molecule.

  • There are six key functional groups to recognize by name and symbol.

  • One of these groups is particularly hydrophobic (does not like water).

  • In organic chemistry, one would delve deeper into their specific tasks; here, we focus on recognition.

1. Hydroxyl Group

  • Symbol: OH-OH

  • Structure: An oxygen atom covalently bonded to a hydrogen atom, with the oxygen then bonding to the main carbon chain.

  • Key Distinction: This is a hydroxyl group, not a hydroxide ion (OH-OH^-). The oxygen is covalently bonded, not negatively charged.

  • Properties: Oxygen needs 22 bonds (one to hydrogen, one to the carbon chain). Hydrogen needs 11 bond (to oxygen).

  • Common Name: Also known as an alcohol when attached to a hydrocarbon.

2. Carbonyl Group

  • Symbol: C=O-C=O

  • Structure: A carbon atom double-bonded to an oxygen atom (C=OC=O).

  • Properties: The oxygen atom is happy (forms 22 bonds). The carbon atom still needs 22 more bonds, which it forms with other atoms in the chain.

  • Distinction: This specifically refers to a carbon double-bonded to an oxygen where the carbon is not also bonded to an OH-OH group (which would make it a carboxyl group).

3. Carboxyl Group

  • Symbol: COOH-COOH or C(=O)OH-C(=O)OH

  • Structure: A combination of a carbonyl group (C=OC=O) and a hydroxyl group (OH-OH) attached to the same carbon atom.

  • Properties: This unique combination of four atoms works together and has specific functional roles in organic molecules.

4. Amino Group

  • Symbol: NH2-NH_2

  • Structure: A nitrogen atom bonded to two hydrogen atoms and one bond to the main carbon structure.

  • Properties: Nitrogen needs 33 bonds to be happy (here, 22 to hydrogens and 11 to a carbon chain).

  • Relevance: This group is crucial in proteins, as it forms a part of amino acids, which are the building blocks of proteins.

    • Note: While it can become ionized (NH<em>3+-NH<em>3^+), for this context, recognition of the NH</em>2-NH</em>2 structure is key.

5. Phosphate Group

  • Symbol: PO4-PO_4

  • Structure: A phosphorus atom bonded to four oxygen atoms (often with both single and double bonds to different oxygens).

  • Relevance:

    • Found in many important biological molecules.

    • Essential for processes involving dehydration synthesis and hydrolysis.

    • Plays a massive role in cellular respiration and the production of ATP (adenosine triphosphate).

6. Methyl Group

  • Symbol: CH3-CH_3

  • Structure: A carbon atom bonded to three hydrogen atoms, with the carbon then bonding to the main chain.

  • Properties:

    • Often found at the end of hydrocarbon chains.

    • Incredibly hydrophobic (hates water) and nonpolar.

    • This property is a primary reason why lipids (like oil) and water do not mix.

Preview of Lipids

  • General Nature: Lipids are a diverse group of organic molecules that primarily do not like water.

  • Types: The four main types include triglycerides, phospholipids, waxes, and steroids.

  • Key Discussions: In this chapter, we will focus on triglycerides (which store energy/fat) and phospholipids (which form cell membranes).

  • Hydrophobic/Hydrophilic Interaction: Lipids generally do not like water, explaining why they orient themselves in specific ways.

    • Phospholipids in cell membranes are depicted as "two-legged jellyfish" with heads that like water (hydrophilic) and tails (containing methyl groups, making them hydrophobic) that face each other, away from water.

    • This orientation creates a barrier that defines the cell's boundaries.