Organic Chemistry Syllabus Overview

Alkanes consist of carbon atoms bonded to each other with single bonds, and each carbon atom forms 4 single bonds.

Alkenes have a carbon-carbon double bond, represented by a C=C bond, introducing unsaturation.

Alkenes have the general formula CnH2n.

The pi bond (π bond) in an alkene is a type of covalent bond formed by sideways overlap of p orbitals. It contains excess electrons and is responsible for reactivity.

Sp2 hybridization describes the bonding in alkenes, where one s orbital and two p orbitals combine to form three equivalent sp2 hybrid orbitals.

Alkynes have a carbon-carbon triple bond (C≡C), making them even less saturated than alkenes.

Benzene is a cyclic, planar structure with delocalized pi electrons within the ring.

Cycloalkanes are cyclic alkanes with the general Formula CnH2n.

An atom or group of atoms within a larger molecule that has a characteristic reactivity, influencing a molecule's behavior in chemical reactions.

An organic compound containing only carbon and hydrogen atoms.

A hydrocarbon derivative where a hydrogen atom is replaced by a halogen (e.g., chlorine, bromine).

A hydrocarbon derivative containing a hydroxyl functional group (-OH).

A systematic method for naming organic compounds, involving parent chain, suffix, prefixes, and locants.

The longest continuous carbon chain in a molecule.

Part of the name indicating the main functional group.

An atom or group of atoms attached to the parent chain, other than the main functional group.

Atoms tend to gain, lose, or share electrons to achieve a full outer electron shell (octet), which is a stable configuration.

Atoms want to achieve the electron configuration of a noble gas, which is a stable configuration.

Electrons in the outermost shell of an atom, involved in chemical bonding.

A step-by-step description of bond breaking and forming in a chemical reaction.

Arrangement of electrons within electron shells of an atom

An electron-rich reagent that forms a bond by donating an electron pair to an electron-poor site.

An electron-deficient reagent that forms a bond by accepting an electron pair from a nucleophile.

A complete and step-by-step account of how an organic reaction takes place.

A long hydrocarbon chain with a carboxylic acid group at one end. Can be saturated or unsaturated.

A lipid that has a phosphate group attached to a glycerol molecule, and two fatty acid chains attached to the other two glycerol carbons.

A lipid formed from a glycerol molecule and three fatty acids.

A fatty acid with single bonds between all the carbon atoms in the hydrocarbon chain.

A fatty acid with one or more double bonds between carbon atoms in the hydrocarbon chain.

Halogens like chlorine (Cl2) and bromine (Br2) readily add across the double bond of alkenes, forming dihaloalkanes.

The addition of halogens to alkenes proceeds through a three-step mechanism involving a cyclic bromonium ion intermediate.

The addition of halogens to alkenes results in the formation of products with an anti (trans) configuration, meaning the halogens are on opposite sides of the molecule.

Hydrogen halides (HX, such as HCl, HBr, and HI) readily add to alkenes, forming haloalkanes.

Carbocation stability increases with the number of alkyl groups attached to the positively charged carbon atom.

In the addition of HX to an unsymmetrical alkene, the hydrogen atom (H) adds to the carbon with more hydrogen atoms already attached, while the halogen (X) adds to the carbon with fewer hydrogen atoms.

A carbon atom that becomes chiral after a reaction, making it identifiable as a new chiral centre.

In the addition of HX to an unsymmetrical alkene, the reaction favors the formation of one specific product over another, determined by Markovnikov's rule.

When HX adds to an alkene, the major product is the one where the hydrogen atom of HX adds to the carbon atom already bonded to the most hydrogen atoms. This is known as Markovnikov's Rule.

HX addition to an alkene occurs with syn addition. This means that the H and X atoms from HX add to the same side of the alkene.

A halohydrin is an organic compound that contains both a halogen (like bromine or chlorine) and a hydroxyl group (-OH) attached to adjacent carbons.

Halohydrins are formed by the addition of hypohalous acids (like HOBr or HOCl) to alkenes. The halogen (X) adds to one carbon, and the hydroxyl (OH) group adds to the other carbon.

Carboxylic acid derivatives have different reactivities towards nucleophilic attack. The reactivity order is: Acid chloride > Acid anhydride > Thioester > Ester > Amide.

The reactivity of carboxylic acid derivatives is influenced by the electron-withdrawing or electron-donating nature of the substituent attached to the carbonyl group. Electron-withdrawing groups increase reactivity, while electron-donating groups decrease it.

The S stands for substitution. In a nucleophilic substitution reaction, a nucleophile (Nu-) replaces a leaving group (LG) on a carbon atom.

A nucleophilic substitution reaction involves the reaction of a nucleophile with a carbon atom carrying a good leaving group. The nucleophile replaces the leaving group, resulting in a new bond formation.

Aldehydes contain a carbonyl group (C=O) where the carbon is bonded to at least one hydrogen atom and one alkyl or aryl group.

The suffix '-al' is used to indicate the presence of an aldehyde functional group in the name of an organic compound.

Ketones contain a carbonyl group (C=O) where the carbon is bonded to two alkyl or aryl groups.

The suffix '-one' is used to indicate the presence of a ketone functional group in the name of an organic compound.

Carboxylic acids contain a carboxyl group (COOH) which is a carbonyl group (C=O) bonded to a hydroxyl group (OH).

The suffix '-oic acid' is used to indicate the presence of a carboxylic acid functional group in the name of an organic compound.

Aromatic hydrocarbons are named by adding 'benzene' after the substituent name. For example, nitrobenzene, chlorobenzene, methylbenzene.

The priority order for naming organic compounds with multiple functional groups is: 1. Carboxylic Acids 2. Aldehydes 3. Ketones 4. Alcohols 5. Amines 6. Alkenes 7. Alkynes 8. Alkanes.

Aromatic hydrocarbons are organic compounds containing a cyclic ring system with delocalized pi electrons. They are characterized by their stability and characteristic scent.

These are terms used to describe the relative positions of two substituents on an aromatic ring. Ortho (o-) indicates substituents on adjacent carbons, meta (m-) on carbons separated by one carbon, and para (p-) on opposite carbons.

Hexoses are simple sugars with six carbon atoms. They are important energy sources in living organisms.

These are two types of sugars classified based on their functional group. Aldoses have an aldehyde functional group at the end of the carbon chain, while ketoses have a ketone functional group within the chain.

This is the type of bond that connects sugar monomers to form polysaccharides (complex sugars). The bond is formed between the anomeric carbon of one sugar and a hydroxyl group of another.

Both are polymers of glucose, but they differ in their glycosidic linkages. Starch has α linkages and is digestible by humans, while cellulose has β linkages and is indigestible.

Amino acids are the building blocks of proteins. They have an amino group (NH2) and a carboxyl group (COOH) attached to a central carbon atom, along with a specific side chain.

A polypeptide is a chain of amino acids linked together by peptide bonds. Many polypeptides fold into functional proteins.

The sugar-phosphate backbone of DNA is hydrophilic, meaning it attracts water molecules, making DNA soluble in water. The nucleobases themselves are hydrophobic, but are shielded within the helix.

Hydrogen bonding between complementary base pairs (A-T, G-C) and hydrophobic interactions between stacked bases play a crucial role in stabilizing the DNA helix.

A long hydrocarbon chain with a carboxylic acid group at one end. Can be saturated (single bonds) or unsaturated (double bonds).

Saturated fatty acids have only single bonds between carbon atoms, while unsaturated fatty acids have at least one double bond. This difference affects their physical properties.

Phospholipids have a hydrophilic phosphate head and hydrophobic fatty acid tails, making them amphipathic. This property allows them to act as surfactants, forming a layer between water and oil.

A nucleophile is an electron-rich species that seeks a positive charge. It forms a new bond by donating an electron pair to an electron-deficient atom.

An electrophile is an electron-deficient species that accepts an electron pair from a nucleophile to form a new bond.

An organic reaction mechanism is a step-by-step account of how a reaction occurs, illustrating the bond breaking and forming, intermediates, and energy changes throughout the process.

The four levels of protein structure are:

1. Primary Structure: The linear sequence of amino acids held together by peptide bonds.
2. Secondary Structure: Local folding of the polypeptide chain into alpha-helices and beta-sheets, stabilized by hydrogen bonds.
3. Tertiary Structure: The overall three-dimensional shape of a single polypeptide chain, formed by interactions between R-groups, including hydrophobic interactions, hydrogen bonds, disulfide bridges.
4. Quaternary Structure: The arrangement of multiple polypeptide chains (subunits) into a functional protein complex, held together by non-covalent interactions.

Enzymes are biological catalysts that accelerate chemical reactions by lowering the activation energy required, bringing reactants together in a specific orientation. They are highly specific and can break down complex molecules like amide bonds.

A covalent bond formed between the carboxyl group of one amino acid and the amino group of another amino acid, releasing a water molecule. It's also known as an amide bond.

A covalent bond formed between two cysteine residues, also called a sulfur-sulfur bond, which helps stabilize the tertiary structure of proteins by creating cross-links.

These interactions are weaker than covalent bonds but crucial for protein structure and function:

• Hydrogen bonds: Occur between a hydrogen atom bonded to a highly electronegative atom like oxygen or nitrogen, and an electronegative atom on another molecule.
• Hydrophobic interactions: Non-polar molecules clump together to minimize contact with water.
• Van der Waals interactions: Weak, temporary interactions between molecules due to fluctuating electric fields.

A molecule that has both a positive and negative charge, but with a net neutral charge. Amino acids exist as zwitterions at neutral pH.

A nucleoside is a molecule composed of a nitrogenous base attached to a pentose sugar, while a nucleotide is a nucleoside with one or more phosphate groups linked to the sugar.

Nucleic acids (DNA and RNA) are made of long chains of nucleotides. Each nucleotide consists of a nitrogenous base (adenine, guanine, cytosine, or thymine/uracil), a pentose sugar (deoxyribose or ribose), and a phosphate group.

The addition of hypohalous acids (HOBr or HOCl) to alkenes, resulting in a compound containing both a halogen and a hydroxyl group on adjacent carbons.

A three-step process involving the attack of the alkene by the electrophilic halogen, formation of a bromonium ion intermediate, and nucleophilic attack of water (or alcohol) on the bromonium ion.

The order of reactivity of carboxylic acid derivatives towards nucleophilic substitution reactions is determined by the electron-withdrawing or donating capability of the substituent attached to the carbonyl group.

Acid halides are the most reactive due to the strong electron-withdrawing nature of the halogen substituent.

Carboxylate ions are the least reactive because their negative charge repels the approach of other nucleophiles.

Reactions where a nucleophile replaces a leaving group on a carbon atom, resulting in the formation of a new bond.

The presence of a good leaving group on the carbon atom facilitates the attack by the nucleophile.

Addition of HX to an alkene occurs with syn addition, meaning both H and X atoms add to the same side of the double bond.

Numbers used to indicate the position of substituents or functional groups on the parent chain.

1. Name the parent cyclic structure (e.g., cyclohex). 2. Add the suffix '-ane' for alkanes. 3. Add a prefix to describe substituents. 4. Include locants to specify substituent positions.

1. Name the parent chain including the double bond. 2. Add the suffix '-ene' for alkenes. 3. Add prefixes for substituents. 4. Include locants for both the double bond and substituents.

1. Name the parent chain. 2. Add the suffix for the functional group. 3. Replace the halogen name with a 'o' ending (e.g., bromine becomes bromo). 4. Include locants for the halogen and other substituents.

1. Name the parent chain. 2. Remove 'e' from alkane name and add 'ol'. 3. Add prefixes for substituents. 4. Include locants for the hydroxyl group and other substituents.

A ranking of functional groups that determines which group is named as the suffix in a molecule with multiple functional groups.

The name of an aldehyde is formed by replacing the 'e' of the parent alkane name with 'al'.

The name of a ketone is formed by replacing the 'e' of the parent alkane name with 'one'.

The name of a carboxylic acid is formed by replacing the 'e' of the parent alkane name with 'oic acid'.

The name of an ester is formed by replacing the 'e' of the parent alkane name with 'ate' and adding the name of the alkyl group attached to the oxygen atom.

A bimolecular nucleophilic substitution reaction where the nucleophile attacks the substrate from the backside, leading to inversion of stereochemistry.

The atom or group of atoms that departs from a molecule during a reaction, often taking its bonding electrons with it.

Alkyl halides' reactivity in SN2 reactions depends on the steric hindrance around the carbon atom. Bulkier groups hinder the nucleophile's approach, decreasing reactivity.

A group that readily departs from a molecule, often because it is stable as a negative ion or can easily stabilize the negative charge.

A good leaving group commonly used in organic synthesis, often formed by reacting an alcohol with tosyl chloride.

The addition of halogens like Cl2 or Br2 to alkenes, forming dihaloalkanes.

The addition of two atoms or groups to the same side of a double bond, resulting in a cis configuration.

The addition of two atoms or groups to opposite sides of a double bond, resulting in a trans configuration.

A cyclic intermediate formed during the addition of halogens to alkenes, with a positive charge on the bromine atom.

The mechanism proceeds in three steps: 1. Electrophilic attack of the alkene by the halogen, 2. Formation of a cyclic bromonium ion intermediate, 3. Nucleophilic attack of water or alcohol on the bromonium ion.