Organic compounds

Composed of C+ H
C-C / C-H bonds

Carbon atom: versatile atom - form 4 covalent bonds

Chains, rings, sheets
Bonds: single/ double / triple

Hydrocarbons: chain of C, H single bonded to C

Alkanes
saturated hydrocarbons - contains ONLY single bonds
CnH2n+2

Full structural diagram

Condensed structural

CH3CH2CH2CH2CH2CH2CH2CH3 Structural formula

3D diagram:

C- tetrahedral → zig zag alignment

Line diagram
point: Carbon
line: bond

Alkyl groups: hydrocarbon attached to main chain → named based off number of carbons attached
 - fragment of alkane formed by removing H
CH3 - methyl group - fragment of methane CH4
Base: octane
Methyl group: propyl

Carbon with methyl group : 5th

5-propyloctane

* number carbons with smallest value

Isomers: different rearrangement of same compound - number of atoms is same

● Occurs with > 3 C atoms

Cyclic alkane : C atoms join to form closed ring

CnH2n
* maximise number of side chains when naming

Alkenes
Unsaturated hydrocarbons - double bonds between C
● Adding hydrogen : saturating the compound
 C=C → C-C (bonded to H)

● Contain min. 1 C=C bond

CnH2n+2-2x
x= number of double bonds

Alkynes
Unsaturated hydrocarbons - triple bonds between C
C(n)H(2n+2-4y)
y= number of triple bonds

Triple bonds do not bend →

CnH2n+2-2x-4y

Naming:
1. Number base C chain
2. Prioritise double/triple bond to give lowest C number
3. Multiple bonds → diene/triene, diyne/triyne
- octa-2,4,6-triene
Side chains
● Halogens - fluoro, chloro, bromo, iodo
● NO2 - nitro
● Benzene - phenyl
● Branched hydrocarbons -propyl/isopropyl/ cyclopropyl

Vinyl : propene

Acetylene : ethyne
 Ethylene : ethene

Cyclic hydrocarbons
single/ double bonds
- Prioritise double bonds
* triple not possible - rigid straight structure - C can only made 4 bonds*
CnH2n-2x

Aromatic hydrocarbons

Benzene rings : Delocalised e- shared amongst carbons in the ring

2 resonance structures → more stable than other double bonded structures

circle = shared delocalised e-

PHENYL : benzene as side group
Naming
1. Name benzene ring
2. Add side groups
Common names
Toluene : methylbenzene
Phenol : hydroxybenzene

o-xylene : 1,2-dimethylbenzene

m-xylene : 1,3-dimethylbenzene

p-xylene : 1,4-dimethylbenzene

TNT: trinitrotoluene
2-methyl-1,3,5-trinitrobenzene

Electrophilic substitution
- benzene reaction
 pi bonds = double bonds
(above/below plane)
Electrons located above/ below plane → creates stable structure
- Is not easily reacted with
Electrophilic substitution: substitution of H in benzene - double bond does not easily break
Electrophile: electron deficient ; accepts e- pairs
pi bonds: high e- density → attract electrophiles

C6H6 + HNO3 C6H5NO2 + H2O

● Concentrated H2SO4 - creates electrophile
● NO2 (Nitro side group) subbing for H
→ H2O product

Isomers
Structural: same formula, different structures
- different chemical/ physical properties
Geometric: same structure, different orientation
● C can rotate/ freedom to move → double bond restricts freedom - no rotation
- C=C must exist
- Both C bonded to different substitutes
 Cis Trans
C chain continues on same side C chain continues on opposing side

cis-but-2-ene trans-but-2-ene

Reactions
Combustion
C o m p l e t e : blue flame
+ O2 → CO2(g) + H2O(g)
- Standard state - H2O (l) , (gas if not specified)

I n c o m p l e t e : orange flame
+ O2 → CO2(g) + CO(g) + C(s) + H2O(l)

● Not very reactive - stable C-C bonds hard to break

- H are replaced instead

Halogenation: substituting hydrogen atom with halogen

● C2H6 + Br2 → C2H5Br + HBr
1-bromoethane + hydrobromic acid
Conditions:
hv: high energy light used to break C-H bond
Δ : heat
● F2 - requires no heat for halogenation -
very reactive
If more Br2(l) present → halogenation continues to occur → more substitution
● C2H6 + Br2 (excess) → C2Br6 + 6HBr

Mechanisms
Free radical chain reaction
Free radical: unpaired electron
● Initiation : producing free radical
- hv light breaks up diatomic molecule into 2 radicals
 ● Homolytic fission: bond will break equally - will receive equal amount of free radicals
● Heterolytic decision: 1 species keeps both electrons

● Propagation : forming products and radicals

- Free radical comes in contact with alkane

● Termination: all remaining radicals are paired - reaction is finished

reactions ~ alkenes/ alkynes

● More reactive than alkanes
double/ triple bonds require less energy to break ; pi bonds broken to form single bond
- Only breaking pi bonds (1 bond)

electrophilic addition ; halogenation:

* no condition required - naturally occurring since double/ triple bond easily broken
Electrophile: electron deficient species - seeking electrons → break double bond

alkenes decolourise bromine water:

Hydrogenation : substituting H2 to break double/ triple bond
● Conditions - heat, pressure, metal catalyst : Ni/Pt/Pd
- H-H bond is stable - requires energy to break

Hydrohalogenation
Electrophile: electron deficient
→ electrophilic species will break double bond

Markovnikov's rule : H atom attaches to C that originally has the most H

- C more polar → more likely to attract H

Nucleophilic substitution
Nucleophiles: electron rich species

Halogenated carbon : δ+ charge

→ attracts nucleophiles (OH-)
OH- replaces halogen

C - partially +ve → attracts -ve species

OH- replaces Br

Hydration : adding H2O

● Condition - strong acid - 6M H+
→ acid facilitates bond breaking - C=C / H-OH

Functional groups
group of atoms that determine characteristics of the compound

Alcohol
contain hydroxyl group -OH
● Functional group: Capable of hydrogen bonding → OH molecule is polar
 R: any carbon chain

Naming:
● Alcohol group has priority over double/triple bond
● Suffix -ol

Methane → methanol
* no number provided - assume on Carbon 1

Butan-2-ol

butane + hydroxyl on 2nd carbon

3,4- difluoro-hex-4-en-2-ol

Prefixes: -diol -triol -tetrol -pentol -hexol

Glycerol :

propane -1,2,3 - triol

CH2OHCHOHCH2OH

Ethyl alcohol :

Ethanol
 Isopropanol :

propan-2-ol

Structural isomers
Based on substitution of carbon attached to OH

C4H9OH - isomers
1. Primary - 1o Bonded C has 2 C-H bonds butanol
1 other carbon bonded

2. Secondary - 2o Bonded C has 1 C-H bond Sec-butanol / 2-butanol

2 other carbons bonded

3. Tertiary - 3o Bonded C has no C-H bonds Tert-butanol

3 other carbons bonded

Isobutanol
Reactions
hydration reaction : Synthesising alcohol
alkene + H2O → alcohol
● EXOTHERMIC : releases energy / no conditions

- markonikov’s rule : C with most H receives H+ (other receives OH-)

- when both C have equal H bonded → 2 products - OH bonded to each

Combustion
CnHxOH + O2 → CO2 + H2O
CnHxOH + O2 → CO2 + CO + C + H2O

Elimination: dehydration reaction - reverse of addition reaction Alcohol → alkene + H2O

● Condition: 12M acid catalyst (concentrated)
● ENDOTHERMIC - requires heat
 * 2 products - markovnikov's rule does not apply backwards

Temperature
Low temp - favours alcohol
High temp - favours alkene

Properties
HIGH melting point
Hydrogen bonding - due to OH group

MP trend
Longer chain → increasing melting point
- Heavier mass

Exponential plateau / differences decrease

SOLUBLE
OH group = polar region = forces formed with H2O
 SOLUBILITY trend
Longer chain → decreasing solubility
Increasing non polar region

Butanol → decanol (basically insoluble in water)

Lucas test : testing structure of alcohol

ZnCl2 (lucas reagent) + concentrated HCl → halogenated alkane + H2O

1o → NO reaction - colourless liquid

RCH2OH + HCl → no reaction

2o → SLOW reaction - white/ cloudy

R2CHOH + HCl → R2CHCl + H2O

3o → FAST reaction - white / cloudy

R3COH + HCl → R3CCl + H2O

Aldehydes
Oxidation of 1o alcohol

1o alcohol → aldehyde

[O] limited : oxidising agent : KMnO4 / K2Cr2O7

- Must be limited to stop oxidisation at creation
of aldehyde
- Alcohol → 1 oxidisation reaction → aldehyde

Must be acidic - balance redox reaction

 - Replacing C-H bond with C=O
- C=O : carbonyl group
Formation
Distillation : makes aldehydes
1. Oxidising agent + alcohol mixture is heated
- Aldehyde : lower boiling point
2. Aldehyde gas rises and condenses to be
collected in flask

Naming:
● Always at end of chain → no need to be numbered
● OH group : hydroxy-

Common names
Formaldehyde : methanal

MP/BP : higher than alkenes, lower than alcohol

IMF: dipole-dipole
● NO H bonding → H not bonded to N,O,F
SOLUBLE
Increase in size → less soluble

Reduction reaction
Aldehyde + H2 → alcohol
● Conditions : metal catalyst + high temp + pressure

Ketones
Oxidation of 2o alcohol
 2o alcohol → ketone

● [O] does not need to be limited - oxidation ends at ketone

carbonyl group in middle of chain

Naming:
Ketone = aldehyde , equal naming priority

Acetone : propanone

Carboxylic acids
Oxidation of 1o alcohol, continuous oxidation
Aldehyde → carboxy
 ● Condition: excess [O] for continuous reaction
- KMnO4 / K2Cr2O7
Formation
Reflux : makes carboxylic acid
1. Distillation
2. Solution is collected to be reacted again

Naming
Prioritised over ketones
-oic acid

Benzoic acid
Formic acid : methanoic acid

Oxalic acid : ethanedioic acid

Acetic acid : ethanoic acid

Citric acid :
2-hydroxy-propane-1,2,3-tricarboxylic acid

Properties

Melting point = HIGH

Dimer: 2 dipole-dipole bonds = stronger
SOLUBLE - OH group
Increase chain → decreased solubility

Carboxylic salt : acid + base → salt + water

Carboxylic acid + YOH → Y - oate

Oxidation of alcohols
Cr2O7 = orange
Cr3+ = green
Cr2(6+) + 6e- (orange) → 2Cr3+ (green)

1o alcohol → oxidised the fastest - dark green

2o alcohol → oxidised
3o alcohol → not oxidised - remains orange
Ethers

-O-

Properties:
MP/BP: lower than alc, higher than alkane
IMF: dipole-dipole

Synthesis reaction
Condensation reaction
Alcohol + alcohol → ether bond + H2O
● Conditions: acidic catalyst/ high temp (130C)

Ester

- COO -
Properties:
MP/BP: larger molecules → higher than ether
IMF: dipole-dipole

Amine
Derivative of ammonia
 Properties
Basic - can be neutralised with acid
MP/BP: HIGH
IMF: H-bonding - stronger
- 3 sites for H bonding
SOLUBLE
- hydrogen bonding with H2O

Synthesis:

Halogenoalkane + (ammonia) ⟶ 1o amine

● Conditions : heat + ethanol catalyst

- Reaction continues with excess haloalkane

 Amides

Properties:
MP/BP : HIGH
IMF: hydrogen - bonding
SOLUBLE
- Hydrogen bonding with H2O

Nitrile

Naming : ending -nitrile

● Side group: cyano-

Properties:
MP/BP: high
IMF: dipole-dipole moment
- no H bonding → no H to bond to N
SOLUBLE - H2O → hydrogen bonding with N

Polymers:
Larger molecules/chains made by linking monomers
- Proteins / carbs / DNA
Properties based on type of linkage/ cross-linking

Addition polymerisatiom : formed by addition reaction

- From monomers w double/triple bonds
- no byproduct/ All atoms form polymer

Polymer notation: n= number of repeating subunits

Homopolymers: made of 1 type of monomer

Heteropolymer: made of 2+ types of monomers

Cross linking : creates covalent bonds between chains

● w/o cross linking - held by london forces/ dipole-dipole attractions
more cross linking → more rigid
 Naming priority:
carb. acid > ester > amide> nitrile> aldehydes=ketones> alcohols> alkene/yne> alkane=amine=ether=halogen

1. carboxylic acid (-oic acid)

2. esters (-oate)
3. amide
4. nitrile (cyano-)
5. aldehydes (-al) / ketones (-one)
6. alcohols (-ol)
7. alkenes / ynes
8. amine (amino) = ether (-oxy-)= halogen
9. alkanes

Functional groups
name pre/suffix Formula Shape IMF MP/BP solubility

Alkane -ane C(n) H(2n+2) London dispersion LOW INSOLUBLE

- linear structure = tightly - non polar
packed

Alkene -ene C(n) H(2n+2+2x) London dispersion LOWer INSOLUBLE

- double bond = kinks →
loosely packed

Alkyne -yne C(n) H(2n+2+4y) London dispersion LOWER INSOLUBLE

Halogens halo- -X- dipole-dipole HIGH SOLUBLE

- dipole bond w H2O
Alcohol -ol -OH- H- bond HIGH SOLUBLE
hydroxy- - OH bonding

aldehyde -al -CHO- Dipole-dipole HIGH SOLUBLE

-oxo- - dipole bond w H2O

ketone -one -CO- dipole-dipole HIGH SOLUBLE

-oxo- - dipole bond w H2O

carboxylic acid -oic acid -COOH- dipole-dipole HIGHer SOLUBLE

- dimer: 2 bonds - dipole bond w H2O

ether -oxy- -O- dipole-dipole HIGH SOLUBLE

- H bond with H2O

ester -oate -COO- dipole-dipole HIGH SOLUBLE

- larger than ether - H bond with H2O

amine -amine -NH2/NH/N- H-bond HIGH SOLUBLE

-amino- - H bond with H2O

amide -amide -CONH- H-bond HIGH SOLUBLE

- H bond with H2O

nitrile -nitrile -CN- dipole-dipole HIGH SOLUBLE

-cyano- - H bond with H2O

Trends

MP/BP:
Larger molecule → HIGHER
- heavier/ more bonds to break

solubility:
Longer chain → DECREASED solubility
- Longer non-polar region

Common names

Vinyl/ propylene : propene

Acetylene : ethyne

Ethylene : ethene

Toluene : methylbenzene

Phenol : hydroxybenzene

o-xylene : 1,2-dimethylbenzene
m-xylene : 1,3-dimethylbenzene

p-xylene : 1,4-dimethylbenzene

TNT: trinitrotoluene
2-methyl-1,3,5-trinitrobenzene

Glycerol :

propane -1,2,3 - triol

CH2OHCHOHCH2OH

Ethyl alcohol :

Ethanol

Isopropanol :

propan-2-ol
Formaldehyde : methanal

Acetone : propanone

Benzoic acid

Formic acid : methanoic acid

Oxalic acid : ethanedioic acid

Acetic acid : ethanoic acid

Citric acid :
2-hydroxy-propane-1,2,3-tricarboxylic acid