PORG Q2 (MIDTERM): Aliphatic Hydrocarbons

alkane, alkene, alkyne

Less dense than water

Insoluble in water

Alkene

Lowest among the three

Alkyne

Highest among the three

petroleum and natural gas

The two most important natural sources of alkanes are ______ and _______

Petroleum

is a complex liquid mixture of organic compounds (alkanes or cycloalkanes).

-formed from the remains of ancient marine organisms (plants, algae, and bacteria) or fossils

Crude oil

Petroleum AKA

Natural gas

often found associated with petroleum deposits, consists mainly of methane (about 80%) and ethane (5% to 10%).

naturally occurring mixture of gaseous hydrocarbons consisting primarily of methane in addition to various smaller amounts of other higher alkanes.

Propane

major constituent of liquefied petroleum gas (LPG), a domestic fuel.

LPG (liquefied petroleum gas)

Propane also known as

LPG (liquefied petroleum gas)

any of several liquid mixtures of the volatile hydrocarbons -propene, propane, butane and butane

Butane (C4H10)

is the gas of choice in some areas.

much safer than propane (indoor usage) -due to higher BP

-42 C

Boiling point of propane

-2 C

Boiling point of butane

insoluble in water

PHYSICAL PROPERTIES of alkanes

polar

nonpolar

water molecules are ______, whereas alkanes are ______ (all the C-C and C-H bonds are nearly purely covalent).

gas, liquid, solid

Physical state

C1-C4

Gas number of carbons

C5-C17

Liquid number of carbons

≥C18

Solid number of carbons

gases, liquids, solids

PHYSICAL PROPERTIES of alkanes

At room temperature, alkanes occur as ______,______and _____ depending on the number of carbons available in the compound

alkanes

Water

mutual insolubility of ______ and _____ is used to advantage by many plants.

Alkanes

often constitute part of the protective coating on leaves and fruits.

Hexane

Famous solvent of alkanes

Alkanes

All of the bonds in _______ are single, covalent, and nonpolar. Hence they are relatively INERT.

ordinarily do not react with most common acids, bases, or oxidizing and reducing agents.

extraction or crystallization

Because of this inertness, alkanes can be used as solvents for ______ or _______ as well as for carrying out chemical reactions of other substances

molecular oxygen, halogens

alkanes do react with some reagents, such as ______ and _____

paraffin

"Lacking affinity"

Other word for alkanes is _____ means _____

Oxidation

Halogenation

Reaction of alkanes (2)

Oxidation

• addition of O, removal of H

• the replacement of C-H bonds by C-O bonds

Halogenation

• one or more hydrogen atoms of the alkane are replaced by halogen (X) atoms

• X - F, Cl, Br, I

Combustion

Famous oxidation in alkanes

fuel

most important use of alkanes is as ______. With excess oxygen, alkanes burn to form carbon dioxide and water.

combustion reactions

are the basis for the use of hydrocarbons for heat (natural gas and heating oil) and for power (gasoline).

initiation step

______is required, usually ignition by a spark or flame.

Once initiated, the reaction proceeds spontaneously and exothermically.

oxygen, heat, fuel

Fire triangle

to make fire to take place there are 3 main ingredients that must be present and this is called ______

EXOTHERMIC

-releases heat - causing temp of the immediate surroundings to RISE

ENDOTHERMIC

absorbs heat -cools the surrounding

partial oxidation

If insufficient oxygen is available for complete combustion of a hydrocarbon, _________ may occur.

*syngas-synthesis gas (mixture of H2 and CO)

Halogenation

• When a mixture of an alkane and chlorine gas is stored at low temperatures in the dark, no reaction occurs.

• In sunlight or at high temperatures, however, an exothermic reaction occurs.

general equation:

R-H+A-B → R-A +H-B

Chlorination

______ of hydrocarbons is a substitution reaction in which a chlorine atom is substituted for a hydrogen atom.

Alkenes

Most reactive among the three

Olefins

Alkene and chloride form oil

Ethyl

Can create 50 organic reaction

C=C ethylene

Simplest form of alkene

Vinyl

Old name/ other name of alkenes

ethene or ethylene

is a plant hormone and an important starting material for the manufacture of other organic compounds.

fruits, steroids, insect pheromones

alkene functional group is found in sources as varied as ___,___,___,citrus

Ethene

Hormone that causes tomatoes to ripen

*plant hormone that can cause seeds to sprout, flowers to bloom, fruit to ripen and fall, and leaves and petals to shrivel and turn brown.

*It is produced naturally by plants from the amino acid methionine.-essential amino acids -cannot be made by the body

Limonene

From lemon and orange oils

B-phellandrene

oil of eucalyptus

multifidene

sex attractant of brown algae

muscalure

sex attractant of the housefly

a-farnesene

found in the waxy coating on apple skins

ETHANOL/ETHYL ALCOHOL

*- CNS depressant/ CNS stimulant

solvent; constituent of cleaning preparations; in synthesis of esters

ETHYLENE CHLORIDE

- 1,2-dichloroethane is used in the production of vinyl chloride monomer (VCM, chloroethene) with hydrogen chloride as a byproduct. VCM is the precursor to polyvinyl chloride.

ETHYLBENZENE

The dominant application of ethylbenzene is its role as an intermediate in the production of polystyrene (Styrofoam)

VINYL CHLORIDE -

VCM is the precursor to polyvinyl chloride.

ETHYLENE OXIDE

ethylene glycol source; surface disinfectant that is widely used in hospitals and the medical equipment industry to replace steam in the sterilization of heat-sensitive tools and equipment, such as disposable plastic syringes.

ETHYLENE GLYCOL

*- antifreeze; Coolant and heat-transfer agent

ACETIC ACID

- otic antibacterial; vinegar

manufacture of vinyl acetate polymers, ethyl acetate solvent and cellulose acetate polymers

VINYL ACETATE

- This colorless liquid is the precursor to polyvinyl acetate and ethene-vinyl acetate copolymers, important industrial polymers

manufacture of poly (vinyl acetate) used in paint emulsions, plywood adhesives and textiles

acetaldehyde

slug killer, in the form of methaldehyde (CH CHO),

polyethylene

"plastic" bags; toys; packaging

isopropyl alcohol

Produced from propylene (propene):

rubbing alcohol; cosmetics; synthesis of acetone

propylene oxide

Produced from propylene (propene):

manufacture of polyurethanes; polyesters

cumene

Produced from propylene (propene):

industrial preparation of phenol and acetone

Isopropylbenzene

Cumene is common name for

polypropylene

Produced from propylene (propene):

molded articles (e.g., kitchenware); fibers for indoor-outdoor carpeting

Alkenes

- They are less dense than water and, being nonpolar, are not very soluble in water.

- , compounds with four or fewer carbons are colorless gases, whereas higher homologs are volatile liquids.

Ethene, propene, butene

exist as colorless gases in alkenes (3)

liquids

Alkenes with 5 to 14 carbons are

solids

alkenes with 15 carbons or more are

SUBSTITUTION

ALKANES most common reaction is

general equation.

R-H+A-B→ R-A+H-B

ADDITION

ALKENES most common reaction is

Hydration

The addition of water to a molecule is called________, so we can say that an alkene will be hydrated in the presence of water and acid.

acid catalyst

Alcohols react with alkenes in the same way that water does. Like the addition of water, the addition of an alcohol requires an _____

Hydrogenation

The addition of hydrogen to alkenes in the presence of a catalyst.

Catalytic hydrogenation

______ of double bonds is used commercially to convert vegetable oils to margarine and other cooking fats.

Unsaturated fats

- heart healthy fats

-plant/fish-based

-usually LIQUID @ room temp

Saturated fats

- SOLID @ room temp

-found mostly in animal-based foods (Meat, butter, milk, cheese)

-Coconut oil, palm oil and cocoa butter (theobroma oil)

SINGLE BONDED COMP

ADDITION OF HALOGEN:

ALKENE + HALOGEN = ____

ALCOHOL

HYDRATION:

ALKENE + H20 W/ ACID CATALYST = ____

ETHER (ROR)

ADDITION OF ALCOHOL :

ALKENE + ALCOHOL = ___

SINGLE BONDS

CATALYTIC HYDROGENATION:

ALKENE + HYDROGEN W/ CATALYST = _____

MARKOVNIKOV'S RULE

the rich get richer. The carbon atom already "rich" in hydrogen atoms gets the extra hydrogen, while the other carbon, relatively "poorer" in hydrogen, gets the halogen. It's all about favoring stability in the resulting product.

Just read

1ST STEP: LOOK FOR DOUBLE BOND

2ND STEP: IDENTIFY WHICH HAS MORE HYDROGEN (CH2)

3RD STEP: BOND H TO CH2

Akynes

There are only a few synthetically occurring alkynes

Acetylene (HC=_CH)

the common name for the smallest alkyne, may be a familiar word because of the oxyacetylene torch used in welding.

is supplied to the torch from one high-pressure gas tank, and oxygen is supplied from another.

Burning acetylene

produces a high-temperature flame capable of melting and vaporizing iron and steel.

capillin, ichthyothereol, enediynes

Alkynes sources

capillin

has fungicidal activity; fungistatic drugs as those that inhibit growth, whereas fungicidal drugs kill fungal pathogens.

ichthyothereol

a convulsant used by the Amazon Indians for poisoned arrowheads.

enediynes

has been found to have powerful antibiotic and anticancer properties.

Shape like kabaong

Parsalmide

- benzamide derivative, anti-inflammatory with analgesic effect

-also possess anxiolytic (reduce anxiety) and tranquilizing properties

Pargyline

- MAO-B inhibitor with anti-HTN

- antihypertensive

Monoamine oxidase-B (MAO-B)

is an enzyme in the body that breaks down several chemicals in the brain, including dopamine.

An MAO-B inhibitor makes more dopamine "FEEL GOOD NT" available to the brain.

Mestranol

is a terminal acetylenic compound that is (17alpha) -17-ethynylestra-1(10),2,4-triene substituted by a methoxy group at position 3 and a hydroxy group at position 17. It has a role as a prodrug and a xenoestrogen. It is a 17beta-hydroxy steroid, a terminal acetylenic compound and an aromatic ether.

Fake estrogen

Xeno estrogen

- insoluble in water

- soluble in solvents with low polarity (benzene and ether)

- less dense than water

- higher boiling point than alkene

Physical properties of alkynes

Electrophilic addition reaction

Alkynes like alkene undergo ____ reaction

Alkynes less reactive than alkene in this reaction

terminal alkyne

If the alkyne is a ________, the H+ will add to the sp carbon bonded to the hydrogen.