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Organic Chemistry - Fundamentals of organic chemistry

Grade 12IBChemistry

Review the key concepts, formulae, and examples before starting your quiz.

🔑Concepts

A homologous series is a group of organic compounds that share the same general formula, have similar chemical properties, and show a gradual change in physical properties. Each member differs from the next by a CH2CH_2 unit.

Physical properties like boiling point increase with the number of carbon atoms due to the increase in London dispersion forces as the molar mass and electron cloud size increase.

Structural isomers are compounds with the same molecular formula but different structural arrangements. This includes chain isomerism, positional isomerism, and functional group isomerism.

IUPAC Nomenclature involves identifying the longest carbon chain (stem), the primary functional group (suffix), and any substituents (prefix). For example, a 4-carbon chain with an alcohol group on the second carbon is named butan2olbutan-2-ol.

Carbon atoms and their attached functional groups (like alcohols or halogenoalkanes) are classified as primary (11^\circ), secondary (22^\circ), or tertiary (33^\circ) based on how many other carbon atoms are bonded to the carbon atom containing the functional group.

The Index of Hydrogen Deficiency (IHD), or degree of unsaturation, indicates the number of rings and/or π\pi bonds in a molecule.

Benzene (C6H6C_6H_6) has a unique structure consisting of a planar hexagonal ring with a delocalized π\pi system. This delocalization provides extra stability, making benzene undergo substitution reactions rather than addition reactions.

Functional groups to identify: Alkanes (CC-C-C-), Alkenes (C=C-C=C-), Alkynes (CC-C\equiv C-), Alcohols (OH-OH), Ethers (O-O-), Aldehydes (CHO-CHO), Ketones (CO-CO-), Carboxylic Acids (COOH-COOH), Esters (COO-COO-), Amines (NH2-NH_2), Amides (CONH2-CONH_2), and Nitriles (CN-CN).

📐Formulae

IHD=12(2c+2hx+n)IHD = \frac{1}{2} (2c + 2 - h - x + n) where cc = Carbon, hh = Hydrogen, xx = Halogen, nn = Nitrogen

CnH2n+2 (General formula for Alkanes)C_nH_{2n+2} \text{ (General formula for Alkanes)}

CnH2n (General formula for Alkenes)C_nH_{2n} \text{ (General formula for Alkenes)}

CnH2n2 (General formula for Alkynes)C_nH_{2n-2} \text{ (General formula for Alkynes)}

CnH2n+1OH (General formula for Alcohols)C_nH_{2n+1}OH \text{ (General formula for Alcohols)}

💡Examples

Problem 1:

Calculate the Index of Hydrogen Deficiency (IHD) for the compound with molecular formula C6H5NO2C_6H_5NO_2.

Solution:

IHD=12(2(6)+250+1)=12(10)=5IHD = \frac{1}{2} (2(6) + 2 - 5 - 0 + 1) = \frac{1}{2} (10) = 5

Explanation:

Using the IHD formula: c=6c=6, h=5h=5, n=1n=1, and x=0x=0. Oxygen is ignored in IHD calculations. An IHD of 5 suggests a benzene ring (IHD=4) and one additional double bond or ring (likely the NO2NO_2 group containing a N=ON=O bond).

Problem 2:

Identify the IUPAC name and the classification (primary, secondary, or tertiary) of CH3CH2C(CH3)(OH)CH3CH_3CH_2C(CH_3)(OH)CH_3.

Solution:

Name: 2methylbutan2ol2-methylbutan-2-ol; Classification: Tertiary (33^\circ)

Explanation:

The longest chain has 4 carbons (butane). The alcohol group and a methyl group are both on carbon 2. The carbon bonded to the OH-OH group is bonded to three other carbon atoms, making it a tertiary alcohol.

Problem 3:

Draw and name two functional group isomers for the molecular formula C3H6OC_3H_6O.

Solution:

  1. CH3CH2CHOCH_3CH_2CHO (Propanal - Aldehyde); 2. CH3COCH3CH_3COCH_3 (Propanone - Ketone)

Explanation:

Both molecules have the molecular formula C3H6OC_3H_6O. Propanal contains the carbonyl group at the end of the chain (aldehyde), while propanone contains the carbonyl group in the middle (ketone).

Fundamentals of organic chemistry - Revision Notes & Key Formulas | IB Grade 12 Chemistry