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Shesh
Organic Chemistry
| Oh | Yeah |
|---|---|
| Water is: | Highly cohesive (high affinity for one another)and polar. |
| Electronegativity: | The measure of the force of an atom's attraction for the electron it shares in a chemical bond with another atom. |
| Electronegativity in the periodic table | From left to right: increasing +ive charges in the nucleus Bottom to top: decrease in the distance of valence electrons from the nucleus |
| Non-polar bonds: | < 0.5 |
| Polar bonds | 0.5 - 1.9 |
| Ionic bonds | > 1.9 |
| ACID | proton donor, produces H3O+ ions in aqueous solutions. |
| BASE | proton acceptor, produces OH- ions in aqueous solutions. |
| Stron acid/base | ----> because equilibrium is far right. |
| pH | -log[H3O+] |
| The LARGER the pKa (small Ka) | the WEAKER the acid |
| The SMALLER the pK (large Ka) | the STRONGER the acid |
| LARGE pKb | STRONG base |
| SMALL pKb | WEAK base |
| When a base accepts a proton | it is converted to its conjugate acid |
| When an acid transfers a proton | it is converted to its conjugate base |
| Buffer solution | weak acid and conjugate base to resist changes in pH |
| Functional groups | - reactive parts of organic molecules - essential for life - same functional groups on compounds allows similar reactivity |
| Alkane | CnH2n+2 chair conformation most stable |
| Alkene | CnH2n |
| TRANS | OPPOSITE |
| CIS | SAME |
| Nomenclature | meth- eth- prop- but- pent- hex- ... |
| Priority | higher atomic number determines priority |
| Alkyl | Alkane - H |
| Alcohol -ol | Hydrogen bonds are weaker than covalent but have a significant effect on properties: - Higher bp than alkanes - more soluble in water both due to (-OH) |
| Amines | 1°, 2°, 3° depending on how many H's have been replaced. -polar - weak bases, aqueous solutions are basic - aliphatic amines ~pKb 3-4 |
| Aliphatic | A class of saturated or unsaturated carbon compounds, in which the carbon atoms are joined in open chains. |
| Aldehydes -al | H-C=O Methanal: 2H's Everything else: 1H & 1C |
| Ketones -one | 2C-C=O |
| Aldehyde & Ketone properties | - higher bp - more soluble in H2O than nonpolar compounds of comparable size |
| Carboxylic Acids -CO2H | - high bp, very strong intermolecular hydrogen bonds - solubility decreases and hydrophobic tail increases - resonance increases acidity |
| Isomer: | different compounds with the same molecular formula |
| Constitutional isomer: | isomer with different connectivity |
| Stereoisomer: | same molecular formula, same connectivity but different orientation so that cannot be interconverted by rotation about a single bond. (different atomic arrangement in space) |
| Enantiomers: | mirror images, non-superimposable. |
| Diastereomers: | non-mirror images. |
| Chiral: | non-superimposable on their mirror image. |
| Achiral: | are superimposable on mirror image. |
| Stereocentre: | Carbon with 4 different groups bonded to it. 2 stereocentres = 2^2 Therefore, 4 stereoisomers. |
| Oxidation: | REMOVAL of electrons or H from an atom and/or ADDITION of O |
| Reduction: | ADDITION of electrons or H to an atom or REMOVAL of O |
| ATP, ADP, AMP | universal carriers of phosphate groups, energy source |
| ATP: | Hydrolysis of terminal phosphate of ATP gives ADP + phosphate + energy |
| NAD/NADH FADH/FADH2 | coenzymes involved in oxidation/reduction of metabolic intermediates |
| NAD+ | an important coenzyme found in cells. It plays key roles as carriers of electrons in the transfer of reduction potential. |
| NADH | reduced form of NAD+ |
| FADH/FADH2 | FADH and FADH2 are reduced forms of FAD. FADH2 is produced in the citric acid cycle. |
| β-oxidation | process by which FA, in the form of Acel-CoA, are broken down to form Acetyl-CoA, the entry molecule for the CAC. |
| β-oxidation [1] | oxidation of C-C to C=C by FAD |
| β-oxidation [2] | hydration of C=C, R enantiomer formed |
| β-oxidation [3] | oxidation of β-hydroxyl group to a carbonyl group by NAD+ |
| β-oxidation [4] | cleavage of C chain by a reverse Claisen condensation (thiolysis) |
| Carbohydrates | - Natural monosaccharides are sweet - Highly soluble MONOS due to the extensive hydrogen bonding between OH groups - tri(number of C)ose(carbohydrate), tetrose, pentose |
| L - | OH LEFT |
| D + | OH RIGHT |
| Haworth projections | Anomeric carbon is the new stereocentre that is formed |
| OH RIGHT | F: down Haworth: α |
| OH LEFT | F: up Haworth: β |
| Mutarotation: | is the change in the rotation between two anomers, α & β. |
| Mattose (di) | α-1,4 - glucosidic bonds |
| Sucrose (di) | α- 1, 2 - glucosidic bonds |
| Unbranched polys | 1,4 α glucosidic bonds |
| Branched polys | 1,4 α glucosidic bonds & 1,6 α glucosidic bonds |
| Starch | 1,4 α glucosidic bonds & 1,6 α glucosidic bonds |
| Cellulose | 1,4 β glucosidic bonds |
| Lipids | -insolubility in H2O due to large hydrocarbon component - saturated: solid/semi-solid - unsaturated: liquid - storage of energy - made of glycerol + 3 FAs |
| Saturated lipids | DECREASE mp as C increases |
| Unsaturated lipids | INCREASE mp as C decreases & C=C decrease |
| Micelle: | spherical arrangement of lipids in water so that hydrophilic head points out, hydrophobic in. |
| Waxes: | are esters formed from long chains of carboxylic acids and alcohols. |
| Phospholipids: | Glycerol + 2FA + phosphoric acid |
| Saponification: | The reaction of an ester with a metallic base and water. |
| Fatty Acids | usually C12-20, unbranched, C-C, C=C (must be cis) |
| Amino acids | Side chains determine their behaviour in water, |
| Isoelectric point (pI): | is pH at which majority of molecules in solution have no nett charge. |
| Electrophoresis | Electrical potential applied, move towards opposite charge. Higher charge density move faster that those with lower charge density. At pI don't move. |
| Peptides read.. | from N terminal |
| Peptides have | trans configuration |
| Peptide or amide bond | -(O=)C-H-N- |
| Primary protein structure | aa sequence |
| Secondary protein structure | folds, α-helices, β-sheets... hydrogen bonding |
| Tertiary protein structures | held together by S-S linkages and other bonds. 3D |
| Quaternary protein structures | Tertiary put together. The arrangement of polypeptide chains into a non covalently bonded aggregation. |
| Hydrophobic effect: | non-polar groups cluster in a way that they are shielded from contact with aqueous environment. |
| Competative inhibition | to active site. |
| Uncompetative inhibition | seperate site to active site but only binds to ES complex. |
| Mixed inhibition | either one, may not affect active site. |
| Precedence | ........... |
| Amino acids | Nitrogen-containing compounds that are the building blocks of proteins. |
| Saccharides | draw.. |
| Saccharides | (Greek σάκχαρον meaning "sugar") are simple molecules that are straight-chain aldehydes or ketones with many hydroxyl groups added, usually one on each carbon atom that is not part of the aldehyde or ketone functional group. |
| Carbohydrates | (CH2O)n |
| Oligosaccharide | 3-6 joined monosaccharides |
| Monosaccharides | ALPHA opposite. BETA same. as CH2OH |
| Cycloalkanes | hex-chair pent-envelope hex-chair |
| Biochemistry of alcohol | Liver oxidises the alcohol to an aldehyde which is toxic. Aldehyde can then be converted into a carboxylic acid which can be used as a source of energy. |
| Amines | are slightly stronger bases than amonia. |
| Carbonyl group | is polar as the oxygen is more electronegative that the carbon |
| Carboxylic acids pKa | 4-5 |
| Carboxacids reaction with bases | whether soluble or insoluble in water react with NaOH, KOH and other strong bases to form WATER-SOLUBLE SALTS. |
| Carboxyl Derivatives - Esters | (R1-C(=O)OR2) condensation bw corboxacid and alcohol. |
| Carboxyl Derivatives - Amides | organic functional group characterized by a carbonyl group (C=O) linked to a nitrogen atom (N), or a compound that contains this functional group |
| Fates of pyruvate: | reduction to lactate or ethanol. oxidation and decarboxylation to acetyl-CoA. |
| Activation of FAs | begins in the cytoplasm with the formation of a thioester. involves a reaction with ATP and then a reaction with coenzyme A, |
| Penultimate carbon: | stereocentre of monosaccharide farthest from carbonyl group |
| Anomer: | pair of cyclic diastereoisomers of a sugar where the position of the OH differs. |
| Cellulose breakdown | humans do not have a β-glucosidase to break cellulose's bonds |
| Glycogen | energy storage in animals. 1,6 or 1,4 α |
| Glycerol | C3H8O3 |
Created by:
nyna
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