PHOrgChem (Lecture) | Module 6 (Part 1: ALIPHATIC, AROMATIC HYDROCARBONS AND ALKYL HALIDES ONLY)

Hydrocarbons

Fundamental in organic chemistry

Hydrocarbons

● Serves as a base for numerous industrial applications, components to pharmaceuticals

Hydrocarbons

● Organic compounds consisting solely of Carbon and Hydrogen

Hydrocarbons

● Found in fuels, medicines, plastics, etc.

Aliphatic Hydrocarbons, and Aromatic Hydrocarbons

Classified into TWO MAJOR GROUPS of HYDROCARBONS that can be categorized into different types

Aliphatic Hydrocarbons

open chain/ straight/branched chains

○ Alkanes, Alkenes, Alkynes

Aromatic Hydrocarbons

ring base/ contains benzene rings

○ Benzene and its derivatives

Hydrocarbon Derivatives

Derivative of Benzene

Hydrocarbon Derivatives

AROMATIC HYDROCARBONS: compounds which contain Oxygen, Nitrogen, Phosphorus, Sulfur or Halogen

Oxygen, Nitrogen, Phosphorus, Sulfur, or Halogen

Hydrocarbon Derivatives is derivative of Benzene which contains?

Hydrocarbon Derivatives Containing Oxygen

HYDROCARBON DERIVATIVES: Alcohols, Phenols, Ether, Ketone, Aldehyde, Carboxylic Acid, Esther, and Acid Anhydride

Hydrocarbon Derivatives Containing Nitrogen

HYDROCARBON DERIVATIVES: Amine, Imine, Amide, and NItriles

Hydrocarbon Derivatives Containing Phosphorus

HYDROCARBON DERIVATIVES: Organophosphates

Hydrocarbon Derivatives Containing Sulfur

HYDROCARBON DERIVATIVES: Thiols, Sulfides, Disulfides, and Sulfoxides

Hydrocarbon Derivatives Containing Halogens

HYDROCARBON DERIVATIVES: Alkyl Halides

Aliphatic Hydrocarbons

HYDROCARBONS: Categorized based on the type of bonding

Aliphatic Hydrocarbons

HYDROCARBONS: Widely used in energy industrial applications, and chemical synthesis

Alkanes

• Saturated hydrocarbons (single bonds).

• Example: Methane (used as fuel and energy source)

CnH2n+2

Chemical Formula of ALKANES

Methane

ALIPHATIC HYDROCARBONS: used as fuel and energy source

Alkenes

• Unsaturated hydrocarbons (double bonds).

• Example: Ethylene (used in plastic production and plant hormone)

CnH2n

Chemical Formula of ALKENES

Ethylene

ALIPHATIC HYDROCARBONS: used in plastic production and plant hormone

Alkynes

• Unsaturated hydrocarbons (triple bonds).

• Example: Acetylene (used in welding and chemical synthesis)

CnH2n-2

Chemical Formula of ALKYNES

Acetylene

ALIPHATIC HYDROCARBONS: used in welding and chemical synthesis

Molecules

The physical state of alkanes depends on their?

Smaller Alkane

PHYSICAL STATE OF ALKANE: they are gases

Larger Alkane

PHYSICAL STATE OF ALKANE: they exists as liquid or solid

Nonpolar

POLAR OR NONPOLAR: Alkane

Insoluble

Alkanes, alkenes, and alkynes are nonpolar, thus the solubility of alkanes to water is?

Soluble

Alkanes alkenes, and alkynes are nonpolar, thus the solubility of alkanes to nonpolar solvents/organic solvents is?

Substitution Reaction

Alkanes undergo what reaction with halogens and other reactive species?

Combustion

It is ia key reaction on Alkanes as it releases energy into the place

Carbon 1 to Carbon 4

LENGTH OF CARBON: Gases, odorless

Carbon 5 to Carbon 17

LENGTH OF CARBON: Liquids

Waxy Solids

Higher alkanes are?

Less

Alkanes are _____ dense than water

Halogenation, Nitration, Sulfonation, and Combustion

Reactions of Alkanes

Halogenation

ALKANES: Reaction with halogens (Cl, Br, I, F).

Nitration

ALKANES: Substitution of hydrogen with nitro (-NO2) group.

Sulfonation

ALKANES: Substitution with sulfonic acid (-SO3H) group

Combustion

ALKANES: Produces CO2 and H2O.

Alkenes

Used in industry applications such as plastics and furniture parts

Alkenes

They are highly reactive due to their double bonds and their reaction forms important industrial compounds like plastics

Alkenes

Boiling points and melting points is lower than alkanes due to their double bonds, increase with molecular weight.

Less

Alkenes are _____ dense than water

Lower Alkenes

PHYSICAL STATE OF ALKANE: they are gases

Higher Alkenes

PHYSICAL STATE OF ALKANE: they are liquids or solids

Hydrogenation, halogenation, hydrohalogenation, and hydration

Addition Reaction of Alkenes

Diols, or Carboxylic Acid

ALKENES: Oxidation, Forms?

Polymerization

ALKENES: Used in plastic production.

• Example: Ethylene polymerizes to polyethylene

Alkynes

More reactive than alkenes due to their triple bonds making them useful in the pharmaceutical industry

Alkynes

Boiling and melting points is higher than alkenes due to their increase molecular interactions

Less

Alkynes are _____ dense than water

Molecular Weight

Physical State of Alkynes Varies With?

Hydrogenation, halogenation, hydrohalogenation, and hydration

Addition Reactions of Alkynes

Carboxylic Acid

ALKYNES: Oxidation, forms?

Propofol

Common Name of 2,6-DIISOPROPYLPHENOL

Propofol

Propofol

ALKANE BASED DRUG:

• Anesthetic

• It is non-polar in nature with allows rapid pain penetration

Halothane, and Dodecane

Other alkane based drugs such as?

Halothane

An inhalation anesthetic—alkane is responsible for its low reactivity and increase stability

Dodecane

Used in spring creams—the alkaneenhances lipid solubility

Isotretinoin

Common Name of (2Z,4E,6E,8E)-3,7-DIMETHYL-9-(2,6,6-TRIMETHYLCYCLOHEX-1-ENYL)NONA-2,4,6,8-TETRAENOIC ACID

Isotretinoin

Isotretinoin

ALKENE BASED DRUG

• Used in acne treatment—the presence of double bonds contributes to its reactivity in cell temperature/exposure

Simvastatin, and Tamoxifen

Other alkene based drugs example are?

Simvastatin

A cholesterol lowering drug—alkene: the double bond affects enzyme interaction

Tamoxifen

A breast cancer treatment—alkene structure influence estrogen receptors binding

Ethylene Estradiol

Common Name of (8R,9S,13S,14S,17R)-17-ETHYNYL-13-METHYL7,8,9,11,12,14,15,16-OCTAHYDRO-6HCYCLOPENTA[A]PHENANTHRENE-3,17-DIOL

Ethylene Estradiol

Ethylene Estradiol

ALKYNE BASED DRUG

• A component of oral contraceptives, the triple bond increases metabolic stability and bioavailability.

Norethynodrel, and Lonafarnib

Other example of alkyne based drugs are?

Norethynodrel

A hormonal medication, the presence of triple bond—alkyne increase bioavailability

Lonafarnib

An anticancer drug, the triple bond—alkyne contributes to enzyme inhibition

Hydrocarbons

Many drugs contain ____________ structures, their physical and chemical properties determine their solubility, stability, and effectiveness in biological systems

Alicylic Hydrocarbons

FORMS RING STRUCTURE BUT DO NOT EXHIBIT AROMATICITY

Carbocylic Hydrocarbons

Alicylic Hydrocarbons is also known as?

Aliphatic Hydrocarbons

Used in Anesthetic, Solvents, and industrial applications due to their stability and chemical properties. (Found in pharmaceuticals, industrial solvents, and fuel additives)

Alicylic Hydrocarbons

Hydrocarbons that form rings but behave like aliphatic compounds.

Cyclopropane

ALICYCLIC HYDROCARBONS: anesthetic gas, used in medical procedures

Cyclohexane

ALICYCLIC HYDROCARBONS: used in the production of nylon and solvents

Cyclopentane

ALICYCLIC HYDROCARBONS: used in insulation and refrigerants

Nonpolar

Alicylic Hydrocarbons are _______, insoluble in water, but soluble in organic solvents.

Alicyclic Hydrocarbons

Boiling and melting points vary with ring size and substituents.

Less

Alicyclic Hydrocarbons are ____ dense than water

Substitution, and Addition

Alicyclic Hydrocarbons undergo _________, and ___________ reactions.

Hydrogenated

Alicyclic Hydrocarbons can be _________ to form alkanes.

Alicyclic Hydrocarbons

Reactivity influenced by ring strain (e.g., cyclopropane is more reactive than cyclohexane).

Ring Strain

Alicyclic Hydrocarbons’ reactivity influenced by _____________ (e.g., cyclopropane is more reactive than cyclohexane).

Smaller

The presence of ring strain (on Alicyclic Hydrocarbons) influences their chemical reactivity making _______ rings more reactive. Their stability, solubility and reactivity is useful in pharmaceutical and industry

Aromatic Hydrocarbons

Contain benzene rings.

Aromatic Hydrocarbons

Examples are Anthracene, Benzo(a)pyrene, Corene.

Aromatic Hydrocarbons

Used in dyes, pigments, and pharmaceuticals.

Aromatic Hydrocarbons

Have delocalized electrons systems making them stable and highly useful in industrial applications

Aromatic Hydrocarbons

Boiling point is higher than alkanes due to strong intermolecular forces

Slightly Soluble

Aromatic Hydrocarbons are nonpolar, they are _______________ in organic solvents.

Aromatic Hydrocarbons

High stability due to resonance structures

Nitration, and Halogenation

Electrophilic Substitution of Aromatic Hydrocarbons