Topic 1 Flashcards by Alex Unknown

Structure of Organic Compounds — Name stems

Meth, Eth, Prop, But, Pent, Hex, Hept, Oct, Non, Dec

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Haloalkane

F, Cl, Br, I

Fluoro-
Chloro-
Bromo-
Iodo-

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Hydroxyl

-OH

-anol or hydroxyl-

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Aldehyde

O
||
—C—H

-anal

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Ketone

O
||
—C—

-anone or oxo-

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Carboxyl

O
||
—C—OH

-anoic acid

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Ester

O
||
—C—O—R’

alkyl -oate

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Amine

-NH₂

-anamine

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Amide

O
||
—C—NH₂

-anamide

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Nitriles

—C=_N

-nitrile or cyano-

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Structure of Organic Compounds — Prefix-stem-suffix

Remember prefixes di, tri, tetra
Remember alphabetical if more than one func group

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Homologous series definition

Same functional group but different number of carbon atoms in the main chain.

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Homologous series trends

Increasing carbons —> increase in electrons available for dispersion forces —> increase in melting and boiling points

Isomerism: Branched reduces surface area when compared to straight.

Polarity affected by chain length, not hydrogen bonding. Only solubility in water is affected.

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Alcohols (properties)

Hydroxyl group can hydrogen bond with water and other alcohols.

Primary > Secondary > Tertiary

Methanol, ethanol and propanol are still soluble in water (not too many hydrophobic parts)

BP, MP increases as chain length increases (more electrons, more dispersion force)

Diols and Triols can have more hydrogen bonding, thus greater MP/BP

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Aldehyde/Ketones (properties)

Carbonyl group can form H bonds with water

First 3 members of homologous series are miscible in water

No H bonds with each other

Ketones have higher BP due to greater dipole-dipole interactions (stronger partial charge)

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Carboxylic acids (properties)

First 4 members of homologous series are miscible in water

Carboxyl group can form 2 H bonds, one from hydroxyl and another from carbonyl
- Higher BP/MP than alcohols
- Stronger hydrogen bonds than alcohols

Can ionise in water, making it very soluble

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Esters (properties)

Methyl methanoate, methyl ethanoate, and methyl propanoate are miscible in water
- polar bond between oxygen and carbon atoms

Lack of hydroxyl group gives similar properties to aldehydes/ketones (lower
melting/boiling point than alcohols and carboxylic acids)

Amines (properties)

Weak base

Primary and secondary amines can hydrogen bond –> comparable boiling points to
aldehydes and ketones due to N-H hydrogen bond being weaker than O-H.

Primary > Secondary > Tertiary

Tertiary has comparable melting and boiling points to hydrocarbons

Beyond fourth member of primary/secondary amines –> miscibility in water drops
off

Amides (properties)

Highest melting/boiling points of any organic compound due to both hydrogen bond
and dipole-dipole capability

Non-bonding electron pair interacts with the oxygen atom to create strong polarity
within molecule –> Very overall polar structure

Tertiary amides do not have hydrogen bonding –> only strong dipole-dipole

More soluble in water than carboxylic acids

Halogens (properties)

Increasing halogen mass = more electron shells/greater atomic mass = more
dispersion = less volatility

Haloalkanes: Higher boiling points than hydrocarbons –> polar interactions
- Heavier halogens = greater dispersion

Triglycerides (Lipids)

Have slightly polar parts and very non-polar parts –> can interact with molecules that are similar
- E.g. propanone has a slightly polar carbonyl group and 2 non-polar methyl groups. This enables the ‘like dissolves like’ rule to apply, where the non- polar parts and the polar parts interact.

However, water is entirely polar, and the non-polar part of triglycerides has a much greater effect than the polar part. This makes triglycerides unable to dissolve in water.

ORP — ADDITION

Adding substituents across a carbon multiple bond (unsaturated molecule) to make a saturated molecule

ORP — Hydrogenation

Adding H₂ to a multiple bond.

Pt/Pd CATALYST : HEAT(150°C) : NO PRESSURE

Alkynes —> H₂ immediately saturates but can use inhibitor to prevent formation of saturated alkane

ORP — Halogenation

Adding diatomic halide Br₂ or Cl₂ to a multiple bond —> dihaloalkane

NO CATALYST : NO HEAT : NO PRESSURE

Alkynes —> dihaloalkene —> haloalkane (4 halogens)

Chemical testing (alkene vs alkane): Bromine agent is orange —> colour disappears during reaction, indicating hydrocarbon is unsaturated

*ORP* — Hydrohalogenation

Adding hydrogen halide molecule HBr or HCl to a multiple bond. NO CATALYST : NO HEAT : NO PRESSURE Markovnikov Rule: Since hydrohalides are asymmetrical, if the unsaturated hydrocarbon is also asymmetrical, different products can form Stipulation: Hydrogen bonds with the (multiple bond) carbon with the most hydrogens, halogen bonds to the carbon with the least hydrogens (90% Markovnikov & 10% non-Markovnikov product)

*ORP* — Hydration

Adding water molecule H2O to carbon double bond. STRONG ACID CATALYST : 300°C : 60atm

*ORP* — Polymerisation

Self addition vs condensation reactions of monomers to form a polymer

*ORP* — Haloalkane elimination (tertiary haloalkane)

Ripping hydrogen halide molecule from two adjacent carbons with Na/K Hydroxide. - higher concentration of hydroxide + higher temperature favours elimination rather than substitution ETHANOL PREDOMINANT SOLVENT : HIGH HEAT : NO PRESSURE Reflux: Reaction vessel condenses evaporated gases to maintain liquid state.

*ORP* — Alcohol elimination (dehydration)

Ripping OH and adjacent hydrogen (H2O) from a primary/secondary alcohol to form an alkene. SULFURIC ACID CATALYST : HIGH HEAT

*ORP* — Oxidation of alcohols

Loss of hydrogen atoms/gain in oxygen atoms (reduction always present, reagent is reduced) Acidified permanganate or dichromate solutions.

*ORP* — Primary alcohol oxidation

Loses two hydrogen to form carbonyl group (aldehyde) Gains one oxygen to form carboxylic acid group Increasing heat favours carboxylic acid production.

*ORP* — Secondary alcohol oxidation

Loses two hydrogen to form carbonyl group (ketone) Cannot be oxidised further as only hydrogens can be replaced.

*ORP* — Permanganate and dichromate colour

Permanganate: Purple —> colourless Dichromate: Orange —> Green

*ORP* — Complete Combustion Reaction vs Incomplete

Fuel + Oxygen to produce Carbon dioxide and water - CONDITIONS: Plentiful supply of oxygen Incomplete: Forms carbon monoxide/carbon instead of CO2

*ORP* — Reduction

Gain of hydrogen atoms/loss of oxygen atoms (oxidation always present, reagent is oxidised) HYDROGENATION Nitrile Reduction: Using lithium aluminium hydride/sodium bromohydride in presence of water to form amine - HIGH PRESSURE : HIGH TEMPERATURE : CATALYST - Hydrogenation also works

*ORP* — Condensation

Two molecules combine to form a bigger molecule + water byproduct Hydroxyl group is dropped by carboxylic acids

*ORP* — Esterification

Carboxyl + alcohol: All components are liquid, included in Kc SULPHURIC ACID CATALYST : HEAT : NO PRESSURE Carboxylic acid forms the main chain, while the alcohol forms the R chain

*ORP* — Ester hydrolysis

Acidic conditions: Proceeds normally and forms full carboxylic acid + alcohol Basic conditions: Incomplete carboxylic acid anion + alcohol

*ORP* — Amide synthesis

Carboxylic acid + amine Tertiary amine cannot form —> hydrogen from amine required to form water from carboxylic acid OH group NO CATALYST : HEAT : NO PRESSURE

*ORP* — Amide hydrolysis

Acidic conditions: Amide + H2O + HCl —> Carboxylic acid + amine

*ORP* — Substitution of alkanes

Replacing a SINGLE hydrogen atom with a halogen - REQUIRES UV LIGHT/HEAT Can be repeated to form a dihaloalkane (replaces another hydrogen) UV light breaks the Cl—Cl into **highly reactive free radicals**

*ORP* — Substitution of haloalkanes

Halogen atom replaced by electron-rich species called a nucleophile. Ethanol solvent, heat Substitution with ammonia can form amine (and ammonium halide byproduct)