Introduction to Organic Chemistry: Hydrocarbons

Flashcards covering key vocabulary terms from the lecture notes on organic chemistry, hydrocarbons, and various functional groups including alcohols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, and amides, along with their properties and reactions.

Organic Chemistry

The study of carbon compounds.

Organic Compounds

Compounds that contain carbon, most of the time hydrogen, and sometimes oxygen, nitrogen, halogens, or sulfur; usually have covalent bonds.

Valence Electrons

Electrons in the highest energy level of an atom, used in chemical bonding.

Hydrocarbons

Organic compounds composed only of carbon and hydrogen.

Methane (CH4)

The simplest hydrocarbon; carbon's four valence electrons are shared with four hydrogen atoms to form an octet for carbon.

Octet Rule

Principle stating that carbon wants 8 valence electrons and hydrogen wants 2 valence electrons.

Single Bond

Sharing of 2 electrons between atoms.

VSEPR theory (4 bonds, no lone pairs)

Predicts a tetrahedral shape for a molecule or compound with four bonds around the central atom and no lone pairs.

Alkanes

Hydrocarbons that contain only carbon-carbon single bonds.

IUPAC System

International Union of Pure and Applied Chemistry system for naming organic compounds.

Straight-chained Alkanes

Alkanes where all carbon atoms are connected in a row, named with an -ane ending and a prefix indicating the number of carbons.

Pentane

An alkane with 5 carbon atoms.

Decane

An alkane with 10 carbon atoms.

Expanded Structural Formula

A structural formula that shows the bonds between all of the atoms in a compound.

Condensed Structural Formula

A structural formula that groups each carbon atom and its attached hydrogen atoms, with subscripts indicating the number of hydrogens.

Skeletal Structures

The simplest structural formulas where carbon and hydrogen atoms are not explicitly shown, but implied by lines and intersections.

Cycloalkanes

Rings made up of all carbon-carbon single bonds; have two fewer hydrogen atoms than corresponding open-chain alkanes.

Cyclopropane (C3H6)

The simplest cycloalkane, with a ring of three carbon atoms bonded to six hydrogen atoms.

Alkane Isomers

Compounds with the same chemical formula but different arrangements of atoms.

Branch (Substituent)

A group not attached to the longest continuous carbon chain in an alkane.

Branched Alkane

An alkane with at least one branch or substituent.

Alkyl Group

An alkane that is missing one hydrogen atom, named with a -yl ending.

Methyl Group (CH3-)

An alkyl group consisting of one carbon atom.

Isopropyl Group (CH3-CH-CH3)

A three-carbon alkyl group where the branching carbon is bonded to the main chain.

Parent Chain (Main Chain)

The longest continuous carbon chain in the IUPAC naming system for alkanes.

Haloalkane

An alkane in which halogen atoms (F, Br, Cl, I) replace one or more hydrogen atoms, named as fluoro, chloro, bromo, or iodo substituents.

Solubility of Alkanes

Alkanes are nonpolar, making them insoluble in water (polar) but soluble in nonpolar solvents.

Unsaturated Hydrocarbons

Hydrocarbons that contain double or triple bonds, having fewer hydrogen atoms than corresponding alkanes.

Saturated Hydrocarbons

Hydrocarbons that contain only single bonds (e.g., alkanes).

Alkenes

Unsaturated hydrocarbons containing at least one double bond between carbon atoms.

Ethene (C2H4)

The simplest alkene, where carbon atoms involved in a double bond are planar.

Alkynes

Unsaturated hydrocarbons containing at least one triple bond between carbon atoms.

Ethyne (C2H2)

The simplest alkyne, where carbon atoms involved in a triple bond are planar.

Cis isomer

An isomer in alkenes where two identical hydrogen atoms or groups, one on each alkene carbon, are on the same side of the double bond.

Trans isomer

An isomer in alkenes where two identical hydrogen atoms or groups, one on each alkene carbon, are on opposite sides of the double bond.

Addition Reactions

Characteristic reactions of alkenes and alkynes where atoms or groups of atoms add to the carbons of the double or triple bond.

Hydrogenation

An addition reaction where hydrogen atoms add to the carbons in a double or triple bond to form alkanes, requiring a catalyst (Pt, Ni, Pd).

Hydration

An addition reaction where alkenes react with water (HOH) in the presence of a strong acid catalyst (e.g., H2SO4) to form an alcohol.

Aromatic Compounds

A family of compounds containing a benzene ring (C6H6), known for distinct odors and less reactivity than typical alkenes.

Benzene (C6H6)

A hydrocarbon consisting of a ring of 6 carbon atoms with one hydrogen atom attached to each, featuring alternating single and double bonds.

Toluene

A common name for 1-methylbenzene, an aromatic compound.

Aniline

A common name for 1-aminobenzene, an aromatic compound.

Phenol

A common name for 1-hydroxybenzene, an aromatic compound with a hydroxyl group attached to an aromatic ring.

Alcohol

An organic compound where a hydroxyl group (-OH) replaces one or more hydrogen atoms in an alkane or cycloalkane, named with an -ol ending.

Ether

An organic compound containing an oxygen atom attached by single bonds to two carbon groups (alkyls or aromatic rings), structured like water or alcohols.

Thiol

A group of sulfur-containing organic compounds that have a sulfhydryl (-SH) group, similar to alcohols.

Methanethiol (CH3-SH)

The simplest thiol.

Primary Alcohol (1° alcohol)

An alcohol where one carbon group is attached to the carbon atom bonded to the hydroxyl (-OH) group.

Secondary Alcohol (2° alcohol)

An alcohol where two carbon groups are attached to the carbon atom bonded to the hydroxyl (-OH) group.

Tertiary Alcohol (3° alcohol)

An alcohol where three carbon groups are attached to the carbon atom bonded to the hydroxyl (-OH) group.

Electronegativity

The ability of an atom to attract electrons towards itself.

Hydrogen Bonding

The attraction between a polarized hydrogen in one molecule and a polarized oxygen, nitrogen, or fluorine in another molecule.

Carbonyl Group

A functional group consisting of a carbon-oxygen double bond (C=O); it is a polar group with partial negative charge on oxygen and partial positive on carbon.

Aldehyde

An organic compound where the carbon of the carbonyl group is bonded to at least one hydrogen atom, named with an -al ending.

Ketone

An organic compound where the carbonyl group is bonded to two alkyl groups or aromatic rings, named with an -one ending.

Dehydration of Alcohols

A reaction where alcohols lose a water molecule when heated with an acid catalyst (e.g., H2SO4) to produce an alkene and water.

Oxidation (organic chemistry)

Generally refers to an increase in the number of carbon-oxygen bonds.

Reduction (organic chemistry)

Generally refers to an increase in the number of carbon-hydrogen bonds.

Oxidation of Primary Alcohols

Usually produces an aldehyde, but can be further oxidized to a carboxylic acid.

Oxidation of Secondary Alcohols

Results in the formation of ketones.

Tertiary Alcohols and Oxidation

Do not oxidize readily because there are no hydrogen atoms on the alcohol carbon.

Oxidation of Aldehydes

Readily oxidizes to carboxylic acids.

Reduction of Aldehydes

Produces primary alcohols, often using NaBH4.

Reduction of Ketones

Produces secondary alcohols, often using NaBH4.

Carboxylic Acid

An organic compound where a hydroxyl group is attached to the carbonyl group, forming a carboxyl group, named with an -oic acid ending.

Carboxyl Group

A functional group consisting of a C=O group with an attached -OH group (-COOH), found in carboxylic acids.

Benzoic Acid

A carboxylic acid derivative of benzene.

Acidity of Carboxylic Acids

Carboxylic acids dissociate in water as weak acids, donating a proton to form a carboxylate ion and a H3O+ ion.

Neutralization of Carboxylic Acids

Carboxylic acids are completely neutralized by strong bases to form water and a carboxylic acid salt.

Carboxylic Acid Salt

Formed from the neutralization of a carboxylic acid, consisting of a carboxylate ion and the metal ion from the base.

Esters

Derivatives of carboxylic acids in which an alkoxy group (-OC) replaces the hydroxyl (-OH) group, often having fruity odors.

Esterification

A reaction where a carboxylic acid reacts with an alcohol when heated in the presence of an acid catalyst to produce an ester and water.

Naming Esters

Consists of two words: the alkyl part from the alcohol, and the carboxylate ion name (replacing -ic acid with -ate) from the carboxylic acid.

Acid Hydrolysis of Esters

Esters are split apart in the presence of a strong acid to produce a carboxylic acid and an alcohol.

Base Hydrolysis of Esters

Esters undergo hydrolysis with a strong base to produce a carboxylic acid salt and an alcohol.

Amines

Derivatives of ammonia (NH3) in which one or more hydrogen atoms are replaced with carbon groups.

Primary Amine (1° amine)

An amine where one carbon atom is directly bonded to the nitrogen atom.

Secondary Amine (2° amine)

An amine where two carbon atoms are directly bonded to the nitrogen atom.

Tertiary Amine (3° amine)

An amine where three carbon atoms are directly bonded to the nitrogen atom.

Aromatic Amines

Amines that use the name aniline as their parent name.

Amines as Bases

In water, amines act as Bronsted-Lowry bases, accepting a proton from water.

Amine Salts

Formed when an amine (base) reacts with an acid, where the nitrogen's lone pair accepts a proton (H+).

Heterocyclic Amine

A cyclic compound that contains one or more nitrogen atoms within its ring structure.

Amides

Derivatives of carboxylic acids in which a nitrogen group replaces the -OH group of the carboxyl group.

Amidation

A reaction where a carboxylic acid reacts with ammonia or a primary (1°) or secondary (2°) amine to produce an amide and eliminate a molecule of water.

Naming Amides (Primary)

Primary amides are named by replacing the -oic acid ending of the corresponding carboxylic acid with -amide.

Naming Amides (Secondary & Tertiary)

Substituent groups on the nitrogen are identified and preceded by the letter N, followed by the parent amide name.

Acid Hydrolysis of Amides

Amides split apart in the presence of a strong acid to produce a carboxylic acid and an ammonium (for 1° amide) or amine salt (for 2° or 3° amide).

Base Hydrolysis of Amides

Amides undergo hydrolysis with a strong base to produce a carboxylic acid salt and ammonia (for 1° amide) or an amine (for 2° or 3° amide).