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__**I. ALKANES **__  Rules:  1. Find and name the parent chain.  2. Determine the side chains and write their names with the use of the suffix "-yl".  3. Determine the carbon atom where the side chains are connected to. This number should be the lowest possible number when starting from just one direction.  4. Separate numbers with a ","  Separate a letter from a number with a "-"  5. If multiple side chains of the same kind are present, use the prefixes "di", "tri", etc.  If multiple side chains of different kinds are present, arrange the side chains in alphabetical order. (do not include prefixes in alphabetization.)
 * A. Naming and Formula Writing **


 * B. Properties **

__Homologous Series: __  - Definition: all the members have the same general formula  - the neighboring members of the series differ by -CH2-, and they show similar chemical properties and a gradation in physical properties - Formula: CnH2n+2 <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- Examples: Methane, ethane, propane, butane, etc. <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- have similar structure <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- insoluble in water <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- non-polar <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- covalently bonded <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- colorless <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- good fuels <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- combustible <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- have london forces / van der Waals

<span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- Methane, ethane, propane, butane: first four are gases at room temperature <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- Pentane, hexane, heptane, ...: fifth to 19th are liquid at room temperature <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- 20th: solid at room temperature (known as paraffin wakes)

<span style="font-family: 'Trebuchet MS',Helvetica,sans-serif; margin: 0px; padding: 0px;">- Trend in Boiling Point: increases as the molar mass of the alkanes increases due to the increase of the van der Waals' attraction between molecules



__<span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">Isomers (Structural) __ <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">- Definition: compounds with the same chemical formula but different structural formula - Examples: Pentane, 2-methylbutane, 2,2-dimethylpropane

Trend in Boiling Point: Decreases as the structure becomes more spherical, as there is less surface area for the intermolecular forces to act




 * <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">C. Reactions **

H 3 -CH 2 -CH 3 + 5 O 2 ——** > ** 3 CO 2 + 4 H 2 O + heat __Two points concerning this reaction are important__: ** 1. **Since all the covalent bonds in the reactant molecules are broken, the quantity of heat evolved in this reaction is related to the strength of these bonds (and, of course, the strength of the bonds formed in the products). Precise heats of combustion measurements can provide useful iinformation about the structure of molecules. ** 2. **The stoichiometry of the reactants is important. If insufficient oxygen is supplied some of the products will consist of carbon monoxide, a highly toxic gas. CH 3 -CH 2 -CH 3 + 4 O 2 ——** > ** CO 2 + 2 CO + 4 H 2 O + heat
 * <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">a) Combustion **
 * b) Chlorine and Bromine **

CH 4 + Cl 2 + energy ——** > ** CH 3 Cl + HCl

Since only two covalent bonds are broken (C-H & Cl-Cl) and two covalent bonds are formed (C-Cl & H-Cl), this reaction seems to be an ideal case for mechanistic investigation and speculation. However, one complication is that all the hydrogen atoms of an alkane may undergo substitution, resulting in a mixture of products, as shown in the following __unbalanced equation__. The relative amounts of the various products depend on the proportion of the two reactants used. In the case of methane, a large excess of the hydrocarbon favors formation of methyl chloride as the chief product; whereas, an excess of chlorine favors formation of chloroform and carbon tetrachloride. CH 4 + Cl 2 + energy ——** > ** CH 3 Cl + CH 2 Cl 2 + CHCl 3 + CCl 4 + HCl The following facts must be accomodated by any reasonable mechanism for the halogenation reaction. ** 1. **The reactivity of the halogens decreases in the following order: F 2 > Cl 2 > Br 2 > I 2. ** 2. **We shall confine our attention to chlorine and bromine, since fluorine is so explosively reactive it is difficult to control, and iodine is generally unreactive. ** 3. **Chlorinations and brominations are normally exothermic. ** 4. **Energy input in the form of heat or light is necessary to initiate these halogenations. ** 5. **If light is used to initiate halogenation, thousands of molecules react for each photon of light absorbed. ** 6. **Halogenation reactions may be conducted in either the gaseous or liquid phase. ** 7. **In gas phase chlorinations the presence of oxygen (a radical trap) inhibits the reaction. ** 8. **In liquid phase halogenations radical initiators such as peroxides facilitate the reaction.

__**<span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">II. ALKENES **__

<span style="font-family: 'Trebuchet MS',Helvetica,sans-serif; font-weight: normal;">- contain a carbon-to-carbon double bond <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif; font-weight: normal;">- form a homologous series with the general formula CnH2n - either non-polar or have very low polarity - like alkanes their boiling points increase as the molar mass increases - insoluble in polar solvents such as water - unsaturated because they can undergo addition reactions across the double bond
 * <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">A. Properties **

1. Combustion
 * B. Reactions**

2. Hydrogenation

3. Halogenation

4. Hydration

5. Polymerization



__**<span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">II. ORGANIC DERIVATIVES **__


 * <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">A. Naming, Functional Groups and Formula Writing **

1. Alcohol <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px; margin: 0px; padding: 0px;">- hydroxy-substituted alkanes, alkenes, or alkynes in which the substitution occurs on a saturated carbon <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px; margin: 0px; padding: 0px;"> - Formula: <span style="font-family: Verdana,Arial,sans-serif; font-size: 12px; line-height: 18px;">R—OH - Classification: based on the class of carbon that the hydroxyl group (-OH) a) Primary: carbon is attached to one other carbon b) Secondary: carbon is attached to two other carbons c) Tertiary: carbon is attached to three other carbons

- Naming: - Examples:
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;">Pick out the longest continuous chain to which the hydroxyl group is directly attached. The parent name of the alcohol comes from the alkane name for the same chain length. Drop the -e ending and add -ol.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;">Number the parent chain so that the carbon bearing the hydroxyl group has the lowest possible number. Place the number in front of the parent name.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;">Locate and name substituents other than the hydroxyl group.

<span style="font-family: arial,helvetica,sans-serif; font-size: 13px; line-height: 19px;">2. Aldehyde <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">- have a carbonyl group (CHO) attached to a hydrogen on one side and an alkyl or aryl group on the other side <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">- Exception: Formaldehyde (simplest form of aldehyde) has a hydrogen on both sides of the carbonyl group <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">- Formula: R-CHO - Naming > > > > >
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Pick out the longest continuous chain of carbon atoms that contains the carbonyl group.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">The parent name comes from the alkane name of the same number of carbons.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Drop the -e ending of the alkane name and add -al.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Number the chain so that the carbonyl carbon has the lower possible number.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Locate and name substituents.

3. Ketone - <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">compounds in which an oxygen atom is bonded to a carbon atom, which is itself bonded to two or more carbon atoms. - Formula: R-COR' (R' represents either the same alkyl group as R or a different alkyl group)

- Naming > > > > >
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Pick out the longest continuous chain of carbon atoms that contains the carbonyl group.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">The parent name comes from the alkane name of the same number of carbons.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Drop the -e ending of the alkane name and add -one
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Number the chain so that the carbonyl carbon has the lower possible number.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Locate and name substituents

4. Carboxylic Acid - <span style="font-family: Verdana,Arial,sans-serif; font-size: 12px; line-height: 18px;">compounds that contain the carboxyl group - Formula: R-COOH - Naming:

> > >
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Pick out the longest, continuous chain of carbon atoms that contains the carboxyl group. The parent name for the compound comes from the alkane name for that number of carbon atoms.
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Change the -e ending of the alkane name to -oic and add the word “acid.”
 * <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 40px; margin-right: 0px; margin-top: 0px; padding: 0px;"><span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Locate and name any substituents, labeling their placement by numbering away from the carboxyl group.

5. Alkyl Halide (AKA Halogen-Substituted Alkane) - <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;"> the carbon atom, which is bonded to the halogen atom, has sp3 hybridized bonding orbitals and exhibits a tetrahedral shape. Due to electronegativity differences between the carbon and halogen atoms, the σ covalent bond between these atoms is polarized, with the carbon atom becoming slightly positive and the halogen atom partially negative. Halogen atoms increase in size and decrease in electronegativity going down the family in the periodic table. Therefore, the bond length between carbon and halogen becomes longer and less polar as the halogen atom changes from fluorine to iodine. - Formula: R-X (X represents F, Cl, Br, I) - Naming: <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">Alkyl halides are named using the IUPAC rules for alkanes. Naming the alkyl group attached to the halogen and adding the inorganic halide name for the halogen atom creates common names.

6. Amine

1. Alcohol
 * <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">B. Properties **

<span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Alcohols contain both a polar —OH group and a nonpolar alkyl group. As a result of this composition, alcohols that have small alkyl chains tend to be water soluble. As alkyl chain length increases, water solubility decreases. <span style="border: 0px initial initial; font-size: 12px; font-style: normal; font-weight: normal; margin-bottom: 0px; margin-left: 0px; margin-right: 0px; margin-top: 5px; padding: 0px;">Through the OH group, alcohols are capable of forming hydrogen bonds to themselves, other alcohols, neutral molecules, and anions. This bond formation leads to abnormally high boiling points compared to other organic molecules of similar carbon chain length.

2. Aldehyde <span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">Like ketones, aldehydes have higher boiling points than hydrocarbons of similar chain lengths due to a greater degree of polarity and greater dipole-dipole interaction between molecules. Carbonyl groups cannot form strong intermolecular hydrogen bonds, so both aldehydes and ketones generally boil at lower temperatures than their alcohol analogues. However, aldehydes and ketones of low molecular weight do form strong hydrogen bonds with water, leading to good solubility.

3. Ketone

<span style="font-family: arial,sans-serif; font-size: 12px; line-height: 15px;">Like aldehydes, ketones have higher boiling points than hydrocarbons of similar chain lengths due to a greater degree of polarity and greater dipole-dipole interaction between molecules. Carbonyl groups cannot form strong intermolecular hydrogen bonds, so both aldehydes and ketones generally boil at lower temperatures than their alcohol analogues. However, aldehydes and ketones of low molecular weight do form strong hydrogen bonds with water, leading to good solubility.

4. Carboxylic Acid 5. Alkyl Halide

__ [|1] __ summarizes data for some representative alkyl halides.

6. Amine


 * <span style="font-family: 'Trebuchet MS',Helvetica,sans-serif;">C. Reactions **
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">1. Combustion of Alcohols **
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">2. Oxidation of Alcohols **
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">- reagents: solution of potassium or sodium dichromate (IV) acidified with dilute sulphuric acid **

- alcohol is first oxidized to aldehyde then further oxidized to carboxylic acid
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">a.) Primary **
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">- oxidized to aldehydes or carboxylic acid depending on the conditions of the experiment **

- oxidized to ketone
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">b.) Secondary **

- no reaction
 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">c.) Tertiary **


 * <span style="font-family: arial,helvetica,sans-serif; font-size: 13px; font-weight: normal; line-height: 19px;">3. Substitution Reaction of Halogenoalkanes with Sodium Hydroxide **


 * Sources**
 * - IB Diploma Program Chemistry Course Companion by Geoffrey Neuss, Oxford University Press**
 * - http://dwb4.unl.edu/calculators/activities/BP.html**
 * - http://www2.chemistry.msu.edu:80/faculty/reusch/VirtTxtJml/funcrx1.htm**
 * - http://www.chemguide.co.uk/organicprops/alkenes/background.html**
 * - http://www.btinternet.com/~chemistry.diagrams/ethene_propene.htm**
 * - http://www.ucc.ie/academic/chem/dolchem/html/dict/alkenes.html**
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 * - http://www.ausetute.com.au/hydraten.html**
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 * - http://www.cliffsnotes.com/study_guide/Introduction-to-Carboxylic-Acids.topicArticleId-23297%2carticleId-23283.html**
 * - http://chemwiki.ucdavis.edu/index.php?title=Wikitexts/UCD_Chem_118B/Chem_118B_Topics/Nomenclature_of_Aldehydes_%26_Ketones**
 * - http://chemcases.com/alcohol/alc-02.htm**
 * - http://www.chemguide.co.uk/organicprops/acids/background.html#top**