Introduction to Organic Chemistry: Hydrocarbons

Flashcards covering key vocabulary terms and definitions from the lecture 'Introduction to Organic Chemistry: Hydrocarbons'.

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 with covalent bonds.

Valence Electrons

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

Hydrocarbons

Organic compounds composed only of carbon and hydrogen.

Methane (CH4)

The simplest hydrocarbon.

Octet Rule

Carbon wants 8 valence electrons, and hydrogen wants 2 valence electrons.

Single Bond

The sharing of 2 electrons between atoms, which count for both atoms sharing them.

VSEPR theory (for 4 bonds, no lone pairs)

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

Alkanes

Hydrocarbons that contain only carbon-carbon single bonds.

IUPAC system

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

Straight-chained or Continuous Alkanes

Alkanes where all of the carbons are connected in a row.

Expanded Structural Formula

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

Condensed Structural Formula

A type of structural formula that shows the arrangement, but each carbon atom and its attached hydrogen atoms are written as a group, with a subscript indicating the number of hydrogen atoms.

Skeletal Structures

The simplest structures drawn for organic compounds, where carbon atoms are not shown (implied at line intersects or ends) and hydrogen atoms are not shown (implied to complete 4 bonds for carbon).

Cycloalkanes

Rings made up of all carbon-carbon single bonds, having two fewer hydrogen atoms than the corresponding open chain alkanes.

Cyclopropane (C3H6)

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

Branch or Substituent

The group(s) not attached to the longest continuous carbon chain in an alkane.

Branched Alkane

An alkane with at least one branch.

Isomers

Two compounds that have the same chemical formula but different arrangements of atoms.

Alkyl Group

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

Main Chain (Parent Chain)

The longest continuous carbon chain in an IUPAC name, which is numbered to give the location of substituents.

Haloalkane

An alkane in which halogen atoms (F, Br, Cl, I) replace one or more hydrogen atoms.

Alkanes (Solubility)

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

Alkenes

Hydrocarbons that contain at least one double bond between carbons, formed when two adjacent carbon atoms share two pairs of valence electrons.

Alkynes

Hydrocarbons that contain at least one triple bond between carbons, formed when two carbon atoms share three pairs of valence electrons.

Unsaturated Hydrocarbons

Alkenes and alkynes, which have fewer hydrogen atoms than corresponding alkanes.

Saturated Hydrocarbons

Alkanes, which contain the maximum number of hydrogen atoms possible.

Ethene (C2H4)

The simplest alkene, whose carbon atoms involved in the double bond are planar or flat.

Ethyne (C2H2)

The simplest alkyne, whose carbon atoms involved in the triple bond are planar.

Cis Isomer

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

Trans Isomer

An alkene isomer where two hydrogen atoms, 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, due to these bonds being easily broken.

Hydrogenation

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

Hydration

A reaction where alkenes react with water (HOH), catalyzed by a strong acid, to form alcohols; H- attaches to the carbon with the most H atoms, and -OH attaches to the other carbon.

Benzene (C6H6)

A hydrocarbon consisting of a ring of 6 carbon atoms with one hydrogen atom attached to each carbon, and alternating single and double bonds, known for being less reactive than typical alkenes.

Aromatic Compounds

Compounds containing a benzene ring, often having distinct odors.

Toluene

The common name for 1-methylbenzene.

Aniline

The common name for 1-aminobenzene.

Phenol

An aromatic compound in which a hydroxyl group (-OH) is attached to an aromatic ring (1-hydroxybenzene).

Alcohol

An organic compound in which a hydroxyl group (-OH) replaces one or more hydrogen atoms in an alkane or cycloalkane.

Ether

An organic compound containing an oxygen atom that is attached by single bonds to two carbon groups (alkyls or aromatic rings), with a C-O-C structure.

Thiols

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

Primary (1°) Alcohol

An alcohol with one carbon group attached to the carbon bonded to the hydroxyl (-OH) group.

Secondary (2°) Alcohol

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

Tertiary (3°) Alcohol

An alcohol with three carbon groups attached to the carbon 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

Consists of a carbon-oxygen double bond (C=O), which is a polar group with a partial negative charge on oxygen and a partial positive charge on carbon.

Aldehyde

An organic compound where the carbon of the carbonyl group is bonded to at least one hydrogen atom.

Ketone

An organic compound where the carbonyl group is bonded to two alkyl groups or aromatic rings.

Benzaldehyde

A benzene derivative that is an aldehyde (C6H5CHO).

Dehydration of Alcohols

A reaction where alcohols lose a water molecule when heated with an acid catalyst (H2SO4) to produce an alkene and water, by removing H- and OH- from adjacent carbon atoms.

Oxidation (in Organic Chemistry)

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

Reduction (in Organic Chemistry)

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

Oxidation of Primary Alcohols

Usually produces an aldehyde, and can also be oxidized further into carboxylic acids.

Oxidation of Secondary Alcohols

Forms ketones.

Oxidation of Tertiary Alcohols

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

Oxidation of Aldehydes

Readily oxidizes to carboxylic acids.

Oxidation of Ketones

Do not undergo further oxidation.

Reduction of Aldehydes

Reduces to give primary alcohols (by NaBH4).

Reduction of Ketones

Reduces to give secondary alcohols (by NaBH4).

Carboxylic Acid

An organic compound in which a hydroxyl group is attached to the carbonyl group, forming a carboxyl group (-COOH).

Benzoic Acid

A benzene derivative that is a carboxylic acid (C6H5COOH).

Carboxylate Ion

An anion produced when a carboxylic acid dissociates in water as a weak acid, donating a proton.

Carboxylic Acid Salt

The product of neutralizing a carboxylic acid with a strong base, 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.

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.

Acid Hydrolysis (Esters)

A reaction where esters are split apart in the presence of a strong acid (H2SO4 or HCl), producing a carboxylic acid and an alcohol.

Base Hydrolysis (Esters)

A reaction where an ester undergoes hydrolysis with a strong base (NaOH or KOH), producing 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 (1°) Amine

An amine in which one carbon is bonded directly to a nitrogen atom.

Secondary (2°) Amine

An amine in which two carbons are bonded directly to the nitrogen atom.

Tertiary (3°) Amine

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

Aniline (Aromatic Amine)

The base name used for aromatic amines (e.g., N-Methylaniline).

Amines as Bases

Amines act as Brønsted-Lowry bases in water, as the nitrogen accepts a proton from water.

Amine Salt

Formed when an amine (base) reacts with an acid (neutralization), where the lone pair of electrons on the nitrogen accepts a proton (H+).

Heterocyclic Amine

A cyclic compound that contains one or more nitrogen atoms within its ring structure, often consisting of five or six atoms.

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 1° or 2° amine to produce an amide, eliminating a molecule of water.

Hydrolysis of Amides (Acid)

When an amide undergoes hydrolysis with an acid, producing a carboxylic acid and an ammonium (for 1° amide) or amine salt (for 2° or 3° amide).

Hydrolysis of Amides (Base)

When an amide undergoes hydrolysis with a strong base, producing a carboxylic acid salt and ammonia (for 1° amide) or amine (for 2° or 3° amide).