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77 Cards in this Set

  • Front
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Properties of Alkanes

- odorless or mild, colorless, tasteless, nontoxic


- nonpolar, insoluble in water but soluble in nonpolar organic solvents, less dense than water


- flammable, otherwise not very reactive

Melting Points and Boiling Points of Alkanes

- 1st 4 = gases at room temp


- 5-15 carbons = liquids


- 16+ = generally low melting, waxy solids


- with ↑ # of C = ↑MP and BP

Alkane Intermolecular Forces

- Contain only nonpolar C-C and C-H bonds


- London dispersion forces

Cycloalkane Properties

- Cyclopropane & cyclobutane are gases at room temp. Larger = liquids and solids


- Nonpolar, insoluble in water, flammable


- More rigid & less flexible = fewer conformers


- Rotation not possible around C-C bonds

Alkanes Formula

CnH2n+2 n=# of carbons

Cycloalkane

Alkane that contains a ring of carbon atoms


- loss of 2H + C-C bond


- CnH2n

Halogenation of Alkanes

- Replacement of an alkane hydrogen by a chlorine or bromine initiated by heat or light


- Only one H at a time is released


CH4 + 4Cl2 →(heat or light) CCl4 + 4HCl

Combustion

- Reaction of an alkane with O2


CnH2n+2 + O2 → CO2 + H2O

Saturated

- Alkanes


- Have as many hydrogens as possible


- Single bonds

Unsaturated

- Alkenes and alkynes


- Contain C-C multiple bonds

Common Names


Ethylene


Propylene


Isoprene


Acetylene

- Ethene


- Propene


- 2-methyl-1,3-butadiene


- Ethyne

Double-bond Shape

- Plane


- No rotation around a double bond,


- Molecules more rigid = alkenes possess ends and sides

Cis Isomer

The 2 groups are on the same side

Trans Isomer

The 2 groups are on opposite sides of the double bond

Cis-Trans isomerism is possible whenever an alkane has...

... 2 different substituent groups on each of its ends

Properties of Alkenes and Alkynes

- Nonpolar, insoluble in water, soluble in nonpolar organic solvents


- Less dense than water


- Flammable, nontoxic


- Alkenes can display cis-trans isomerism


- Chemically reactive at the multiple bond

Addition Reaction

- X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product

Elimination Reaction

- Saturated reactant yields and unsaturated product by losing groups from two adjacent atoms

Substitution Reaction

- An atom or group of atoms in a molecule is replaced by another atom or group of atoms


- Has to be energetically favorable


AB+C→AC+B

Rearrangement Reaction

- A molecule undergoes bond reorganization to yield an isomer


- Needs a catalyst (H2SO4)

Hydrogenation

- Alkenes and Alkynes react with hydrogen in the presence of a metal catalyst to yield corresponding alkane product

Halogenation

- Alkenes and alkynes react with halogens to yield 1,2-dihaloalkane addition products


- Need a catalyst

Hydrohalogenation

Alkenes react with hydrogen bromide to yield alkyl bromides and with hydrogen chloride to yield alkyl chlorides.



Most reactions of C-C multiple bonds are_____

Addition reactions

Markovnikov's rule

In the addition of HX to an alkene, the major product arises from the H attachment to the double bond carbon that has the larger # of H atoms directly attached to it.

Hydration Reaction

Alkenes won't react with water alone, need a strong acid catalyst for an addition reaction to occur yielding an alcohol.

The more carbons attached to carbocation...

...the more stable it will be, making the formation more favorable


Tertiary = Most stable


Secondary = 2nd most stable


Primary = Very Unstable

Polymer

Large molecule formed by repetitive bonding together of many smaller molecules called monomers

Polymerization

- Simple alkenes undergo polymerization reactions when treated with proper catalyst

Initiator

- Polymerization reaction begins with the addition of an initiator to an alkene = results in the breaking of one of the bonds making the double bond

Aromatic

The class of compounds containing benzene-like rings

Benzene Properties

- Flat symmetrical molecule


- Much less reactive than alkenes and normally don't undergo addition reactions


- Causes cancer by going right in-between DNA


- Simple aromatic hydrocarbons are nonpolar, insoluble in water, volatile, and flammable

Resonance

- Each C-C bond is intermediate between a single bond and a double bond


- All C-C bonds in benzene are identical - Double bond electrons are free to move around molecule = Stability

Nitration (Benzene)

- Substitution of Nitro group for a hydrogen on an aromatic ring


- Strong Acid (H2SO4)

Halogenation (benzene)

- Halogenation substitution of Halogen group for a hydrogen on an aromatic ring


- FeCl3 or FeBr3 Catalyst

Sulfonation

Substitution of a sulfonic acid group (SO3H) for a hydrogen on an aromatic ring


- H2SO4

Alcohols are derived from...

... water, structural similarity also leads to similarities in physical properties.

Methyl Alcohol (Methanol)

- CH3OH


- Wood alcohol (heating wood in absence of air)


- Used as a solvent and a starting material for preparing formaldehyde


- Colorless, miscible with water, and toxic. Blind=low doses Death=high doses

Ethyl Alcohol (Ethanol)

- CH3CH2OH


- Grain alcohol


- Alcohol you drink


- Fermentation=startches and sugars broken down and converted into monomers=ethyl alcohol by yeast enzymes


- Maximum Alcohol concentration = 14% unless distilled = denatured alcohol that is toxic

Ethanol + gasoline

- commercially available to start combustion (engine) faster.

How is Industrial Ethanol made

made by the hydration of ethylene. Yields 95% ethyl alcohol plus 5% water - subsequent removal of water = 100% alcohol

Isopropyl Alcohol

- Rubbing Alcohol (CH3)32CHOH


- Used as a 70% mixture with water as a rubdown and in astringents, as a solvent, a sterilant, and skin cleanser


- Less toxic than methyl alcohol but much more toxic than ethanol

Ethylene Glycol

- a diol HOCH2CH2OH


- colorless liquid that is miscible with water and insoluble in nonpolar solvents


- Used as an engine antifreeze and coolant and as a starting material for the manufacture of polyester films and fibers such as dacron


- highly toxic with slightly sweet taste - phased out in favor of propylene glycol

Propylene Glycol

- CH3CH(OH)CH2OH


- Tasteless and nontoxic


- Replaces Ethylene Glycol as a coolant

Glycerol (Glycerin)

- Triol glycerol


- HOCH2CH(OH)CH2OH


- Colorless liquid that is miscible with water


- nontoxic, sweet taste - useful in candy and prepared foods.


- Used in cosmetics as a moisturizer, in plastic manufacture, in antifreeze and shock-absorber fluids, and as a solvent


- Extremely viscous fluid because of Hydrogen bonds

Diols

2 OH groups on adjacent carbons are glycols


- only reserved for ethylene gylcol and propylene glycol

Alcohols are polar because of...

...electronegative oxygen atom

Straight chain alcohols _____are liquid

with up to 12 carbons

Methanol and Ethanol are...

miscible with water and can dissolve small amounts of ionic compounds

All alcohols have both a _____ part and a _____ part

Hydrophilic part (alcohol) and a Hydrophobic part (hydrocarbon)

Dehydration

Alcohols undergo loss of water on treatment with a strong acid (elimination reaction)

Major product of dehydration

Major product has the greater # of alkyl groups directly attached to the double bond carbons

Oxidation

Increase C-O and Decrease of C-H

Primary Alcohols are converted into...

...aldehydes under controlled conditions


...carboxylic acids if an excess of oxidant is used

Secondary Alcohols are converted into...

...ketones on treatment with oxidizing agent

Tertiary Alcohols with oxidizing agents...

can't react because there isn't a hydrogen on the carbon

Carbolic acid

Phenol itself - medical antiseptic that numbs the skin

alkyl-substituted phenols like cresols(methylphenols) are...

common disinfectants

Phenol Properties

- Influenced by electronegative oxygen and hydrogen bonding

- Most are water-soluble and have higher MP and BP than similar alkylbenzenes

- Less soluble in water than alcohols

- Many biomolecules contain hydroxyl-substituted benzene ring

- Used in medicine

ortho (o-)


meta (m-)


para (p-)



- 1,2


- 1,3


- 1,4

Methanol and Ethanol dissociate so little in water that their aqueous solutions are....

Neutral

Alcohols and phenols are _______ because of positively polarized OH hydrogen

weakly acidic

Alkoxide Ion

- Anion of an alcohol (RO-) (carbon chain with dissociated alcohol)


- Strong base as a hydroxide ion


- Produced by reaction of an alkali metal with an alcohol

The bigger the alcohol....

the faster they dissociate = Oxygen keeps Ions

Phenols are about________times more....

10,000 times more acidic than water and normal alcohols

Phenoxide Ion is produced by the reaction of...

...a phenol with dilute aqueous sodium hydroxide


Phenol in water = acid

Phenols =

Antioxidant

- OR group on ethers =

alkoxy group (methoxy and ethoxy)

Ethers (hydrogen bonding)

Ethers don't form hydrogen bonds to one another

Ethers Properties

- Higher BP than alkanes but lower than alcohols


- Alkane-like in many properties and don't react with acids, bases, or other reagents


- Simple ethers = highly flammable (lots of oxygen = explosive


- Found in plant oils, perfumes, and manufacturing of medicine.

Water solubility of ethers

the oxygen atom in ethers can hydrogen bond with water, causing ethers with smaller organic groups to be more water soluble than with larger organic groups


- Make good solvents for reactants where a polar solvent is needed but no -OH groups can be present

Thiols

- Sulfur analogs of alcohols (SH)

Thiols Properties

- Appalling odor (Skunk/Sliced Garlic and Onion)


- Natural gas is odorless - methanethiol added to make leak detection easy

Thiols react with mild oxidizing agents to yield.....

...disulfides


- 2 thiols join, the hydrogen from each is lost and a bond forms between the sulfurs

Thiols occur in the amino acid...

... cysteine, which is a part of many proteins

The proteins in hair are...

...unusually rich in S-S and S-H groups

Alkyl halides

Simplest Halogen-containing compounds