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77 Cards in this Set
- Front
- Back
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 |
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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 |
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Alkane Intermolecular Forces |
- Contain only nonpolar C-C and C-H bonds - London dispersion forces |
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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 |
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Alkanes Formula |
CnH2n+2 n=# of carbons |
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Cycloalkane |
Alkane that contains a ring of carbon atoms - loss of 2H + C-C bond - CnH2n |
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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 |
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Combustion |
- Reaction of an alkane with O2 CnH2n+2 + O2 → CO2 + H2O |
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Saturated |
- Alkanes - Have as many hydrogens as possible - Single bonds |
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Unsaturated |
- Alkenes and alkynes - Contain C-C multiple bonds |
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Common Names Ethylene Propylene Isoprene Acetylene |
- Ethene - Propene - 2-methyl-1,3-butadiene - Ethyne |
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Double-bond Shape |
- Plane - No rotation around a double bond, - Molecules more rigid = alkenes possess ends and sides |
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Cis Isomer |
The 2 groups are on the same side |
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Trans Isomer |
The 2 groups are on opposite sides of the double bond |
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Cis-Trans isomerism is possible whenever an alkane has... |
... 2 different substituent groups on each of its ends |
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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 |
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Addition Reaction |
- X-Y adds to the multiple bond of an unsaturated reactant to yield a saturated product |
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Elimination Reaction |
- Saturated reactant yields and unsaturated product by losing groups from two adjacent atoms |
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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 |
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Rearrangement Reaction |
- A molecule undergoes bond reorganization to yield an isomer - Needs a catalyst (H2SO4) |
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Hydrogenation |
- Alkenes and Alkynes react with hydrogen in the presence of a metal catalyst to yield corresponding alkane product |
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Halogenation |
- Alkenes and alkynes react with halogens to yield 1,2-dihaloalkane addition products - Need a catalyst |
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Hydrohalogenation |
Alkenes react with hydrogen bromide to yield alkyl bromides and with hydrogen chloride to yield alkyl chlorides. |
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Most reactions of C-C multiple bonds are_____ |
Addition reactions |
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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. |
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Hydration Reaction |
Alkenes won't react with water alone, need a strong acid catalyst for an addition reaction to occur yielding an alcohol. |
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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 |
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Polymer |
Large molecule formed by repetitive bonding together of many smaller molecules called monomers |
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Polymerization |
- Simple alkenes undergo polymerization reactions when treated with proper catalyst |
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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 |
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Aromatic |
The class of compounds containing benzene-like rings |
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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 |
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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 |
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Nitration (Benzene) |
- Substitution of Nitro group for a hydrogen on an aromatic ring - Strong Acid (H2SO4) |
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Halogenation (benzene) |
- Halogenation substitution of Halogen group for a hydrogen on an aromatic ring - FeCl3 or FeBr3 Catalyst |
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Sulfonation |
Substitution of a sulfonic acid group (SO3H) for a hydrogen on an aromatic ring - H2SO4 |
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Alcohols are derived from... |
... water, structural similarity also leads to similarities in physical properties. |
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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 |
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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 |
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Ethanol + gasoline |
- commercially available to start combustion (engine) faster. |
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How is Industrial Ethanol made |
made by the hydration of ethylene. Yields 95% ethyl alcohol plus 5% water - subsequent removal of water = 100% alcohol |
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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 |
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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 |
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Propylene Glycol |
- CH3CH(OH)CH2OH - Tasteless and nontoxic - Replaces Ethylene Glycol as a coolant |
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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 |
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Diols |
2 OH groups on adjacent carbons are glycols - only reserved for ethylene gylcol and propylene glycol |
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Alcohols are polar because of... |
...electronegative oxygen atom |
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Straight chain alcohols _____are liquid |
with up to 12 carbons |
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Methanol and Ethanol are... |
miscible with water and can dissolve small amounts of ionic compounds |
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All alcohols have both a _____ part and a _____ part |
Hydrophilic part (alcohol) and a Hydrophobic part (hydrocarbon) |
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Dehydration |
Alcohols undergo loss of water on treatment with a strong acid (elimination reaction) |
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Major product of dehydration |
Major product has the greater # of alkyl groups directly attached to the double bond carbons |
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Oxidation |
Increase C-O and Decrease of C-H |
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Primary Alcohols are converted into... |
...aldehydes under controlled conditions ...carboxylic acids if an excess of oxidant is used |
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Secondary Alcohols are converted into... |
...ketones on treatment with oxidizing agent |
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Tertiary Alcohols with oxidizing agents... |
can't react because there isn't a hydrogen on the carbon |
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Carbolic acid |
Phenol itself - medical antiseptic that numbs the skin |
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alkyl-substituted phenols like cresols(methylphenols) are... |
common disinfectants |
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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 |
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ortho (o-) meta (m-) para (p-) |
- 1,2 - 1,3 - 1,4 |
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Methanol and Ethanol dissociate so little in water that their aqueous solutions are.... |
Neutral |
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Alcohols and phenols are _______ because of positively polarized OH hydrogen |
weakly acidic |
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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 |
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The bigger the alcohol.... |
the faster they dissociate = Oxygen keeps Ions |
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Phenols are about________times more.... |
10,000 times more acidic than water and normal alcohols |
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Phenoxide Ion is produced by the reaction of... |
...a phenol with dilute aqueous sodium hydroxide Phenol in water = acid |
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Phenols = |
Antioxidant |
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- OR group on ethers = |
alkoxy group (methoxy and ethoxy) |
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Ethers (hydrogen bonding) |
Ethers don't form hydrogen bonds to one another |
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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. |
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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 |
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Thiols |
- Sulfur analogs of alcohols (SH) |
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Thiols Properties |
- Appalling odor (Skunk/Sliced Garlic and Onion) - Natural gas is odorless - methanethiol added to make leak detection easy |
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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 |
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Thiols occur in the amino acid... |
... cysteine, which is a part of many proteins |
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The proteins in hair are... |
...unusually rich in S-S and S-H groups |
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Alkyl halides |
Simplest Halogen-containing compounds |