Organic Chemistry (Nomenclature)

aliphatic hydrocarbons

Long carbon chains (straight or cyclic) surrounded by hydrogen. They contain single, double, or triple bonds between carbons.

organic compound

Carbon-containing compounds.

* Any of a large class of chemical compounds in which one or more atoms of carbon are covalently linked to atoms of other elements, most commonly hydrogen, oxygen, or nitrogen

inorganic compound

Does not contain C atoms.

* Exceptions: CO2, carbides, carbonates, cyanides

carbon

The “element of life”: it bonds with a variety of elements in a variety of shapes, is an excellent building block due to strong bonds that are able to re-arrange themselves

alkanes

A class of hydrocarbon compounds that **consist entirely of atoms of carbon and hydrogen** bonded to one another by *carbon-carbon* and *carbon-hydrogen* __**single bonds**__.

* **- ane**

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* **Not soluble** in __water__; **soluble** in __non-polar__ solvents
* **Density** is __less than that of water__
* **Boiling point** __increases__ as the __size__ of the chain __increases__
* **London Forces!!**

alkyl groups

Smaller carbon chains attached as __**branches**__ to the parent.

* methyl, ethyl, etc.

location numbers

The longest carbon chain (parent) is numbered to show on to which carbon a branch (alkyl group, functional group) is attached. If there are multiple branches on a parent chain, numbering starts on the end closest to the branch with the highest priority.

alkenes

A class of hydrocarbons with **at least one** *carbon-to-carbon* __**double bond**__.

* **- ene**

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* Slightly more reactive than alkanes due to the double bonds

alkynes

A class of hydrocarbons which contain at least one *carbon-carbon* __**triple bond**__.

* **- yne**

enynes

When there is a double bond and a triple bond in the same compound!

Number from the end closest to either the double or triple bond; if there’s a choice, __**the double bond gets priority**__ (lowest #)!!

* **root - # - en - # - yne"**

isomer

Molecules that have the same molecular formula, but their atoms are in __different arrangement__.

structural isomers

Molecules that have the SAME molecular formula, but their atoms are bonded together in a DIFFERENT sequence.

* Physical properties, such as boiling points, vary, as do their shapes.

stereoisomers

Molecules that have the SAME molecular formula and their atoms are bonded together in the SAME sequence, but DIFFER in the 3D orientations of their atoms in space.

* Alkenes have double bonds that are flat and rigid because their atoms cannot rotate around the double bond.
* Two types: diastereomers and enantiomers

diastereomers

**** only for alkenes! ****

Each carbon atom involved in the DOUBLE BOND has DIFFERENT types of atoms or groups of atoms bonded to it.

The double bond prevents rotation around the carbon atoms, resulting in __two separate orientations in space__.

Two types of orientation: *cis* (D or Z) and *trans* (E)

cis

The two larger or smaller atoms or groups are on the SAME side of the double bond (above or below the bond plane).

trans

The two larger or smaller atoms or groups are on OPPOSITE sides of the double bond (one above and one below the bond plane).

enantiomers

**** only for a single carbon!! ****

Mirror images of each other around a SINGLE CARBON atom bonded to __four DIFFERENT types of atoms or groups__.

They are ***non-superimposable*** mirror images of each other (have different spatial arrangement).

* For example, our hands!

alkyl halide hydrocarbons

Has at least __one halogen side group__.

* Generally colourless and odourless compounds
* They are hydrophobic in nature
* __Boiling point__ is higher than alkanes if the number of carbon atoms is the same in both

nitro hydrocarbons

Has at least __one nitro side group__.

cyclic hydrocarbons

General formula: C*n*H*2n, r*epresented by POLYGONS.

* *** If you have one that is not the main chain, then you name it as a branch! The ending is changed to “yl”.**

aromatic hydrocarbons

Have a BENZENE ring, C*6*H*6* - a six carbon, six hydrogen ring with alternating single & double bonds.

* All six carbon-carbon bonds are intermediate in length between a single and double bond due to resonance (delocalized electrons are shared by all six carbon atoms).

benzene

C*6*H*6*, a six carbon, six hydrogen ring with alternating single & double bonds.

phenyl

***** **If you have a benzene ring attached to a straight or cyclic hydrocarbon chain that is larger than the ring itself (more than 6 carbon atoms), the benzene ring is the side group and you name it as a branch!**

alcohols

Contains a __hydroxyl group__ (-OH) attached to a carbon chain (NOT hydroxide; the -OH group is covalently bonded rather than ionically bonded).

* Higher boiling points than haloalkanes that remain associated with intermolecular hydrogen bonding

phenol

A __hydroxyl group__ (-OH) attached to a benzene ring.

ethers

An oxygen atom bonded to two carbon atoms by single bonds.

* **“-oxy”** ending

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* The boiling point is comparable to alkanes but much lower than that of alcohols of comparable molecular mass despite the polarity of the C-O bond

aldehydes

At least one H atom is attached to a carbonyl group (on the end of a carbon chain).

* Have __strong odors__
* Are __polar compounds__
* Only dipole-dipole interactions (NO hydrogen bonding)
* __Low boiling points__ compared to amines and alcohols, higher than hydrocarbons
* __Soluble__ in water (not soluble in nonpolar compounds)

ketone

Two carbon groups are attached to a carbonyl group (in the middle of a chain).

* Have __pleasant odors__
* Are __polar compounds__
* Only dipole-dipole interactions (NO hydrogen bonding)
* __Low boiling points__ compared to amines and alcohols, higher than hydrocarbons
* __Soluble__ in water (not soluble in nonpolar compounds)

carboxylic acids

**** TOP OF PRIORITY SHEET!!!!! **** → will ALWAYS be the parent group if they are present.

Contains a __carboxyl group__, which is a carbonyl group attached to a hydroxyl group (-COOH).

The common names use prefixes “form- and “acet-” for the first two carboxylic acids.

* The carboxyl group contains __three__ __**polar covalent bonds**__: C=O, C-O, and O-H; so they are __**polar**__
* Have __higher boiling points__ than other types of organic compounds (with the same molecular weight) because of __**hydrogen bonding**__
* __More soluble__ (!!!) in water than alcohols, ethers, aldehydes, and ketones because of __**stronger hydrogen bonding**__
* Liquid forms have __sharp and disagreeable odors__
* __THEY TASTE SOUR__ (exist in pickle, lime, and lemon)

esters

**** FAVOURITE ON TESTS & EXAMS, LOTS OF REACTIONS!!!! ****

**** 2nd ON PRIORITY LIST ****

The H in the carboxyl group of a carboxylic acid is replaced with an alkyl group.

* Give flowers and fruits their pleasant fragrances and flavours.

hydrolysis

Reaction with water; breaking a bond and adding the elements of water.

amines

Organic derivatives of ammonia (NH*3*), in which one or more alkyl, cycloalkyl, or aromatic groups replace hydrogen and bond to the nitrogen atom.

Classified as primary, secondary, and tertiary (similar to alcohols) → __the__ __**number of carbon groups**__ that are bound to the nitrogen atom.

The **-NH*****2*** group of a primary amine can be thought of as an **“amino group”** (a BRANCH).

* State: tend to be **gases** for low molecular weight cases, many **heavier ones** are **liquids** are room temperature
* Tend to exhibit **strong odors**, some have a “fishy” smell!
* __Boiling points__ are intermediate to those for alcohols and alkanes of similar molar mass; because of the presence of **N-H** bonds in primary + secondary, *H-bonding is sometimes possible;* however, because __***N is not as electronegative as O, the N-H bond is not as polar as an O-H bond***__ (hence __***weaker H-bonding***__)
* Tend to be **water-soluble** because of H-bonding interactions with water molecules; in fact, those with fewer than six carbon atoms are infinitely water-soluble
* Water-solubility decreases as chain length increases and as the **degree of N-substitution increases**

amides

Possess a functional group that consists of a __**C=O (carbonyl) directly bonded to a nitrogen atom**__.

Classified as primary, secondary, and tertiary.

* The simplest ones are **liquids** at room temperature, and all unbranched having 2 or more carbons on their C-chain side are **solids**
* Secondary and tertiary have lower melting points, with tertiary amides having lower melting points than secondary amides (__***less opportunity for H-bonding)***__*.*