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Organic Chemistry: Structure, synthesis and design


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Organic Chemistry: Structure, synthesis and design


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Rahil Mehta



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Organic Chemistry: Structure, synthesis and design - Details

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Alkanes
-chain of carbons connected by single bonds -ane -CnH2n+2
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Meth-
One carbon
NA
NA
Eth-
Two carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Pro-
Three carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
But-
Four carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Pent-
Five carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Hex-
Six carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Hept-
Seven carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Oct-
Eight carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Non-
Nine carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Dec-
Ten carbons
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Cycloalkanes
-CnH2n -carbon atoms forming a ring -Numbered starting at the point of greatest substitution -Prefix: Cyclo-
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Alkenes
R-C=C-R -ene -contain carbon-carbon double bonds
NA
NA
Alkynes
R-C≡C-R -yne -carbon-carbon triple bonds
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Haloalkanes
-contains halogen -F, Cl, Br, I -can also be named as alkyl halides
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Alcohol
Hydroxyl (-OH) -replace "-e" of corresponding alkane with -ol. Pre: Hydroxy- Suff: -ol
Carboxylic Acid
Pre: carboxy- Suff: -oic acid
Ester
Carboxyl group in between chain (R-C(=O)-OR') Pre: alkoxycarbonyl- Suff: -oate
Amide
Amino group and carbonyl group (R−C(=O)−NR′R″) Pre: amido- Suff: -amide
Nitrile
Nitrile (−C≡N) Pre: cyano- Suff: -nitrile
Aldehyde
Carbonyl at end of a chain (R-C=O) Pre: oxo- Suff: -al
Ketone
Carbonyl in between a chain (R−C(=O)−R') Pre: oxo- Suff: -one
Amine
Amino group (R-NH2) Pre: amino- Suff: -amine
Halide
-I, -Br, -Cl, -F Pre: halo-
Carboxylic Acids
Carbonyl and hydroxyl Pre: Carboxy- Suff: -oic acid
Stereoisomer
Isomers which have the atoms bonded to the same carbon but differ in their spatial arrangement
Positional Structural Isomer
When a the parent chain is the same but the position of the functional group changes
Chain Structural Isomer
Different branching within a carbon chain with the same molecular formula (butane and 2-methylpropane)
Cis Isomer
Bonded to same side of C=C Pre: Cis-
Trans Isomer
Bonded to opposite sides of C=C Pre: Trans-
Monosaccharide
Carbohydrates made up of only one sugar unit
Glucose
A monosaccharide that is the primary form of carbohydrate used to provide energy in the body
Fructose
A monosaccharide found in fruit
Galactose
A monosaccharide found in milk
Disaccharide
A carbohydrate made up of two sugar units
Sucrose
A disaccharide made from glucose and fructose (table sugar)
Polysaccharide
A carbohydrate made up of many sugar units linked together
Amylose
Simplest starch that is a long unbranching chain of glucose molecules
Amylopectin
A branched-chain (more complex) type of starch composed of glucose units
Oligosaccharide
A carbohydrate made up of 3 to 10 sugar units, some of which cannot be digested
Resistant starch
Starch packed too tightly to be digested in GI tract
Soluble fiber
Fiber that dissolves in water
Insoluble fiber
Fiber that will not dissolve in water
1,4 Alpha Bond
Chemical bond between the first carbon on one glucose to the fourth carbon on the second glucose molecule.
1,6 Alpha Bond
Chemical bond between the first carbon molecule on one glucose to the sixth carbon on the second glucose molecule.
Beta bond
Type of chemical bond that cannot be broken by human intestinal enzymes during digestion when it is part of a long chain of glucose molecules.
Starch
Carbohydrate made of multiple units of glucose attaches together in a form the body can digest; also known as complex carbohydrate.
Glycogen
Carbohydrate made of multiple units of glucose with a highly branched structure; sometimes known as animal starch.
Cellulose
Straight chain polysaccharise of glucose molecules that is indigestible because of beta bonds; part of soluble fiber.
Condensation
Chemical reaction in which a bond is formed between 2 molecules by the elimination of a small molecule (like water).
Lactose
A disaccharide that consists of the sugars glucose and galactose
Maltose
A disaccharide composed of two glucose molecules.
Glycolysis
Breakdown of glucose
Alkene → alkane
H₂ and nickel catalyst, (reduction reaction/hydrogenation)
Alkene → polyalkane
Several monomers of the alkene, high pressure, catalyst, (addition polymerisation)
Alkene → dihaloalkane
Br₂, F₂ and Cl₂, room temperature, (electrophilic addition)
Alkene → haloalkane
HBr, HCl, HI, room temperature, (electrophilic addition)
Alkene → alcohol
H₂O, high temperature, H₃PO₄ catalyst, (hydration)
Alkane → haloalkane
UV light, heat, Br₂, Cl₂, I₂, (free radical substitution)
Haloalkane → amine
NH₃ in ethanol, heat under pressure (nucleophilic substitution)
Haloalkane → nitrile (extending the carbon chain)
KCN in ethanol, heat (nucleophilic substitution)
Haloalkane → alcohol
NaOH under reflux (heat) in a 50:50 ethanol to water solution (nucleophilic substitution)
Alcohol → ester
Carboxylic acid, concentrated H₂SO₄ and heat (esterification)
Secondary alcohol → ketone
H⁺/K₂Cr₂O₇, KMnO₄ reflux (heat), (oxidation)
Primary alcohol → aldehyde
H⁺/K₂Cr₂O₇ or KMn, distill immediately, gentle heat (oxidation)
Aldehyde → carboxylic acid
Excess H⁺/K₂Cr₂O₇, reflux (heat), (oxidation)
Carboxylic acid → ester
Alcohol and concentrated H₂SO₄ and heat, (esterification)
Nitrile → amine
LiAlH₄ (hydride reduction)
Carboxylic acid → amide
Amine (condensation)
Haloalkane → dihaloalkane
Br₂, Cl₂, I₂ and UV (again) (Addition)
Haloalkane → alkene
NaOH and heat (elimination)
Amine → amide
Carboxylic acid (condensation)
Ester → alcohol
Water and Base
Ester → carboxylic acid
Water and base (hydrolysis) produces alcohol too
Monosaccharide
Carbohydrates made up of only one sugar unit
Glucose
A monosaccharide that is the primary form of carbohydrate used to provide energy in the body
Fructose
A monosaccharide found in fruit
Galactose
A monosaccharide found in milk
Disaccharide
A carbohydrate made up of two sugar units - joined with a glycosidic bond
Lactose
A disaccharide that consists of the sugars glucose and galactose
Maltose
A disaccharide composed of two glucose molecules.
Sucrose
A disaccharide made from glucose and fructose (table sugar)
Polysaccharide
A carbohydrate made up of many sugar units linked together