hydrocarbon derivative

-Organic compounds are divided into two main classes: hydrocarbons and hydrocarbon derivatives
-Hydrocarbon derivatives are molecular compounds of carbon and at least one other element that is not hydrogen
-Organic halides are organic compounds in which one or more hydrogen atoms have been replaced by halogen atoms
-Common organic halides include freons (chlorofluorocarbons) and Teflon (polytetrafluoroethylene)
-Naming halides uses the same format as branched-chain hydrocarbons
-The branch is named by shortening the halogen name to fluoro-, chloro-, bromo-, or iodo-
-In drawing organic halides using IUPAC names, draw the parent chain and add branches at locations specified in the name
eg.

    Cl Cl
     | |
   H-C-C-H
     | |
     H H


1,2-dichloroethane

-Organic halides react fast which is explained from the idea that no strong covalent bond is broken – the electron rearrangement does not involve separation of the carbon atoms
-Addition of halogens could be added to alkynes which results in alkenes or alkanes
-By adding halogens to alkenes, the product could undergo another addition step, by adding halogens to the parent chain, the double bond has to become a single bond in order to accommodate the halogens
eg.

 Br Br              Br Br
  | |                | |
H-C=C-H + Br-Br => H-C-C-H
         | |
                    Br Br

-By adding hydrogen halides to unsaturated compounds will produce isomers

  H H H               H H H                    H H H
  | | |               | | |                    | | |
H-C=C-C-H + H-Cl => H-C-C-C-H       OR       H-C-C-C-H  
      |               | | |                    | | |
      H              Cl H H                    HCl H

-Substitution reaction is a reaction that involves the breaking of a carbon-hydrogen bond in an alkane or aromatic ring and the replacement of the hydrogen atom with another atom or group of atoms
-With light energy it enables the substitution reaction to move at a noticeable rate eg. C₃H₈ + BR₂ + light => C₃H₇Br + HBR
-Through substitution reaction, in order to name the reaction product, just indicate the location number of the replacement, followed by the halogen prefix (eg. Bromo-) and then state the type of parent chain. Also indicate the second product created from substitution reaction (hydrogen bromide) eg. propane + bromine => 1-bromopropane + hydrogen bromide
-Elimination is an organic reaction in which an alkyl halide reacts with hydroxide ion to produce an alkene by removing a hydrogen and halide ion from the molecule

  H H H             H H H
  | | |             | | | 
H-C-C-C-H + OH => H-C=C-C-H + H-O + Br
  | | |                 |       |
  H BrH                 H       H

-Alcohols have properties that can be explained by the presence of a hydroxyl (-OH) functional group attached to a hydrocarbon chain
-Short-chain alcohols are very soluble in water because they form hydrogen bonds with water molecules
-Alcohols are used as solvents in organic reactions because they are effective for both polar and non-polar compounds
-To name alcohols, the –e is dropped from the end of the alkane name and is replaced with –ol eg. Methane => methanol
-Methanol is also called wood alcohol because it was once made by heating wood shavings in the absence of air
-These days, methanol is prepared by combining carbon monoxide and hydrogen at high temperatures and pressure with the use of a catalyst
-Methanol, however, is poisonous to humans. Consuming a small amount could cause blindness or death
-When naming alcohols with more than two carbon atoms, the position of the hydroxyl group is indicated
-Alcohols that contain more than one hydroxyl group are called polyalcohols, their names indicate the positions of the hydroxyl groups eg. 1,2-ethanediol
-Alcohols undergo elimination reactions to produce alkenes through being catalyzed by concentrated sulfuric acid, which removes or eliminates a hydrogen atom and a hydroxyl group

  H H                  H H 
  | |                  | |
H-C-C-H  + acid  =>  H-C=C-H   +   H-O
  | |                                |
  H OH                               H


ethanol + acid => ethene   + water

-Ethers is a family of organic compounds that contain an oxygen atom bonded between two hydrocarbon groups, and have the general formula R₁-O-R₂
-To name ethers add oxy to the prefix for the smaller hydrocarbon group and join it to the alkane name of the larger hydrocarbon group
eg.

CH3-O-C2H5  


methoxyethane

-Ethers have low solubility in water, low boiling points, and have no evidence of hydrogen bonding
-Ethers undergo chemical change only when treated with powerful reagents under vigorous conditions
-Ethers are formed by the condensation reaction of alcohols
-Condensation reaction is the joining of two molecules and the elimination of a small molecule, usually water
-The carbonyl functional group, -CO-, consists of a carbon atom with a double covalent bond to an oxygen atom
-Aldehydes has the carbonyl group on the terminal carbon atom of a chain
-To name aldehydes, replace the final –e of the name of the corresponding alkane with the suffix –al
-Small aldehyde molecules have sharp, irritating odors whereas larger molecules have flowery odors and is used to make perfumes
-A ketone has the carbonyl group present anywhere in a carbon chain except at the end of the chain
-The difference in position of the carbonyl group affects the chemical reactivity, and enables us to distinguish aldehydes from ketones empirically
-To name ketones, replace the –e ending of the name of the corresponding alkane with –one
-The simplest ketone is acetone (propanone), CH₃COCH₃
-The family of organic compounds, carboxylic acids contain the carboxyl functional group, -COOH, which includes both the carbonyl and hydroxyl groups
-Carboxylic acids are found in citrus fruits, and other foods with properties of having a sour taste
-Carboxylic acids also have distinctive odors (like sweat from a person’s feet)
-The molecules of carboxylic acids are polar and form hydrogen bonds both with each other and with water molecules
-Carboxylic acids acid properties, so a litmus test can separate these compounds from other hydrocarbon derivatives
-To name carboxylic acids, replace the –e ending of the alkane name with –oic, followed by the word “acid”
-Methanoic acid, HCOOH, is the first member of the carboxylic acid family
-Some acids contain two or three carbonyl groups such as oxalic acid, and citric acid

 
    COOH  CH2-COOH
    |   |
    COOH             HO-C-COOH
   |
   CH2-COOH

     

oxalic acid      citric acid

-When carboxylic acids undergo a condensation reaction, in which a carboxylic acid combines with another reactant, it forms two products – an organic compound and water
-Esterification is the condensation reaction in which a carboxylic acid reacts with an alcohol to produce ester and water
-carboxylic acid + alcohol => ester + water
-The ester functional group is similar to that of an acid, except that the hydrogen atom of the carboxyl group is replaced by a hydrocarbon branch
-Esters are responsible for the odors of fruits and flowers and are also added to foods for aroma and taste
-To name an ester, determine name of the alkyl group from the alcohol used in the esterification reaction
-Next change the ending of the acid name from “–oic acid” to “–oate”
-ethanoic acid + methanol => methyl ethanoate + water
-Artificial flavorings are made by mixing synthetic esters to give similar odors of the natural substance
-An amide consists of a carboxyl group bonded to a nitrogen atom
-Amides could be formed in condensation reactions
-Amides occur in proteins, the large molecules found in all living organisms
-Peptide bonds is the joining of amino acids together in proteins
-To name amides, have the name of the alkane with the same number of carbon atoms, with the final –e replaced by the suffix –amide
-Change the suffix of the carboxylic acid from “–oic acid” to –amide to have the same name results eg. ethanamide
-Amines consist of one or more hydrocarbon groups bonded to a nitrogen atom
-Through X-Ray diffraction reveals that the amine functional group is a nitrogen atom bonded by single covalent bonds to one, two, or three carbon atoms
-Amines are polar substances that re extremely soluble in water as they form strong hydrogen bonds both to each other and to water
-Amines have peculiar, horrible odors (eg. smell of rotting fish)
-The name of amines include the names of the alkyl groups attached to the nitrogen atom, followed by the suffix –amine eg. methylamine
-Amines with one, two, or three hydrocarbon groups attached to the central nitrogen atom are referred to as primary, secondary, and tertiary
-Primary amines is when a hydrogen atom attached to the nitrogen atom is replaced by a hydrocarbon group
-Secondary amines are when two hydrocarbon groups replaces the hydrogen atoms and tertiary amines replaces all of the hydrogen atoms with hydrocarbon groups
-Amines are used in the synthesis of medicines
-A group of amines found in many plants are called alkaloids
-Many alkaloids influence the function of the central nervous systems of animals
-Substitution – alkane/aromatic + halogen + light => organic halide + hydrogen halide
-Elimination – alkyl halide + OH => alkene + water |+ water + halide ion
-Elimination – alcohol + acid => alkene + water