L5: Carbon compounds & isomerisation Flashcards
Define functional groups
Specific combinations & geometries of heteroatoms
Define heteroatoms
Any atom that is NOT a carbon or hydrogen
What is the primary focus of organic chemistry?
Carbon-containing compounds
What are constitutional isomers?
Molecules with the same molecular formula but different connectivity
What are hydrocarbon frameworks in organic compounds?
Basic skeletons composed of carbon and hydrogen atoms
What is the significance of carbon chains in organic chemistry?
They provide the structural framework for diverse molecules
What distinguishes alkenes from alkanes?
Alkene has a carbon-carbon double bond
Alkane has a C-C triple bond
What are aryl groups?
Substituents derived from an aromatic ring
How do alkyl groups function in organic chemistry?
They serve as substituents
How do functional groups contribute to the properties of organic molecules?
They determine a molecule’s chemical properties
What is the relationship between molecular structure and boiling points in alkanes?
Increased branching decreases boiling points
Define isomers
molecules with the same molecular formula but different 3D structures
name 2 main groups of isomers
1) constitutional isomers
2) stereoisomers
difference between constitutional isomers & stereoisomers
constitutional isomers differ in their chemical bonding
stereoisomers have identical bonding patterns, but spatial arrangments differ
Why is chirality important in the context of thalidomide?
Chirality results in different enantiomers having distinct therapeutic effects
What is a racemic mixture?
A mixture containing equal amounts of enantiomers
What is the importance of IUPAC rules in naming organic compounds?
They ensure a universal and unambiguous naming convention
How do D and L labels relate to biological molecules?
Indicate stereoisomer configuration
What are atropisomers, and how do they arise?
Stereoisomers resulting from restricted rotation about a single bond
What defines chirality in molecules?
Having a non-superimposable mirror image
What historical example illustrates the importance of chirality in pharmaceuticals?
The thalidomide tragedy
What defines a chiral center in a molecule?
An atom bonded to four different chemical groups
What 3 techniques can be used to characterize organic molecules?
NMR, Mass Spectrometry, and IR
What is the role of stereoisomerism in organic compounds?
Affecting the biological activity of organic compounds
What is optical activity and how do chiral compounds exhibit it?
The rotation of polarized light, exhibited by molecules lacking internal symmetry
What is the difference between E/Z nomenclature and cis/trans labeling?
E/Z is applicable to all alkenes
cis/trans is limited to disubstituted alkenes
How does cis-trans isomerism affect the properties of a molecule?
It affects the physical and chemical properties
What is the significance of diastereomers in stereochemistry?
They have different physical and chemical properties, enabling separation and differentiation
Why are enantiomers significant in biological systems?
They may exhibit different biological activity because biological systems are stereospecific
What role do lipids play in biological systems?
Providing insulation, energy storage, and cell structure
What is the difference between R and S nomenclature in stereochemistry?
R is “clockwise” and S is “counterclockwise” based on substituent priority
How can you determine the configuration of a chiral center using the Cahn-Ingold-Prelog system?
By assigning priorities and tracing a path with the lowest priority group pointing away from you
What are enantiomers and how do they behave in chiral environments?
Non-superimposable mirror images that behave differently in chiral environments
What does chirality mean?
‘Mirror-image, non-superimposable molecules’
How does thalidomide demonstrate the concept of racemisation?
Thalidomide undergoes rapid interconversion between its enantiomers in vivo
How do phospholipids contribute to membrane structure?
They form a bilayer with hydrophobic tails inward
What are glycerolipids and how are they formed?
Lipids with a glycerol backbone formed by esterification with fatty acids
What is keto-enol tautomerism and why is it significant in biology?
A reversible interconversion between keto and enol forms, influencing DNA stability and enzymatic reactions
