The study of Carbon and its compounds Organic Chemistry The study of Carbon and its compounds

Properties Solubility Most nonpolar (like dissolves like) O H O

Properties Electrolytic Behavior Covalent, no conductivity (an exception is organic acids)

Properties Melting/ Boiling Points Low due to weak forces of attraction between molecules (Van der Waals)

Properties Rate of Reaction Slower than inorganic compounds High activation energy

Properties C Bonding Nonpolar covalent Carbon has 4 valance electrons- tetrahedron Carbon can bond with itself indefinitely (in dif. shapes, many variations) Always make 4 bonds C

Homologous Series

Alkanes Single-bonded hydrocarbons Hydrocarbon= only carbon and hydrogen atoms IUPAC name Molecular Formula Generic Formula methane CH4 ethane C2H6 propane C3H8 butane C4H10 pentane C5H12 hexane C6H14 CnH2n+2 heptane C7H16 octane C8H18 nonane C9H20 decane C10H22 As the molecular size and dispersion forces increase, the boiling point and freezing point increase

Isomers Although these structures look different, they both have the same molecular formula of C4 H10 Compounds with: the same molecular formulas different structural formulas C4 H10 Normal Butane 2-Methyl Propane

Alkenes have one Double-bonded hydrocarbon Unsaturated Same prefix as alkanes, with suffix -ene Dienes contain TWO double bonds, and are not alkenes!

Benzene 6 carbon atoms in a ring Aromatic Hydrocarbon Only structure really needs to be known for the regents.

Alkynes one Triple-bonded hydrocarbon Unsaturated Same prefix as alkanes, and alkenes, with suffix -yne

Table Q

Single Bonds Double/Triple Bonds

Alkyl Groups Have 1 less hydrogen (H) than the corresponding alkane Ex: Methyl CH3 1 less H than CH4 Ethyl C2H5 1 less H than C2H6 2-Methyl Propane 3-ethylpentane

Draw

Drawing Rules Step 1 Step 2 Step 3 It’s as easy as 1, 2, 3…. -ane, Alkane: draw all single bonds -ene, Alkene: except draw a double on the number carbon that is present in the name -yne, Alkyne: except draw a triple bond on the number carbon that is present in the name Make sure all carbons have 4 bonds

1st Task: Draw Hexane CCCCCC Condensed Formula: CH3-CH2-CH2-CH2-CH2-CH2-CH3 1st Task: Hexane -ane = only single bonds Hexane CCCCCC

2nd Task: Draw 1-Pentene 5 4 3 2 1 1 2 3 4 5 -ane, Alkane: 5 4 3 2 1 -ane, Alkane: draw all single bonds -ene, Alkene: except draw a double on the number carbon that the prefix shows -yne, Alkyne: except draw a triple bond on the number carbon that the prefix shows 2nd Task: -ene, Alkene: draw all single bonds except draw a double on the number carbon that the prefix shows 1 2 3 4 5

3rd Task: Draw 2-butyne -ane, Alkane: draw all single bonds -ene, Alkene: except draw a double on the number carbon that the prefix shows -yne, Alkyne: except draw a triple bond on the number carbon that the prefix shows 3rd Task: -yne, Alkyne: draw all single bonds except draw a triple bond on the number carbon that the prefix shows 1 2 3 4

Draw: 2, 3-dimethylbutane

Practice Problems Why? General formula Structure Name Using Table Q, what type of homologous structure is this and why? Why? General formula Structure Name

Organic compounds and their functional groups Table R Organic compounds and their functional groups

Halides (Halocarbons) A halide is formed when one or more halogen elements attach themselves to a chain of carbons atoms Halogen include all the elements in group 17

H H H H C C C H H Naming Halocarbons Halocarbons are usually formed from Alkenes This is because the double bonds that are present break; leaving empty bonds on the carbons where the halogens are now able to form H H H H C C C H H Double Bond

1,2-DiFluoropropane H H H H C C C H H F F Naming Halocarbons Every halogen has its own prefix to put at the beginning of its name It is listed in Table R When the bonds brake;the halogens fill the empty space 1,2-DiFluoropropane H H H H C C C H H F F

Alcohols Contain 1 less Hydrogen and in its place there is an –OH group instead. Even though alcohols have an –OH group, they are not a considered a base. This is because there are covalent bonds holding the –OH to the carbons and bases don’t have covalent bonds present on the –OH. When in solution, acids only release and H+ and bases release OH- H H H C C H H H O H

H H Ethanol H C C H O H H H Naming Alcohols You start with Alkane. (In this case, Methane) Take away one of the Hydrogen atoms. Add an –OH group to the empty space For the name; drop the –e at the end of the prefix (Methane) and add –ol to name the Alcohol! H H Ethanol H C C H O H H H

Ether In an ether, there is always an oxygen atom in between two carbons. And there can be any number of carbons on each side of the oxygen. H H H H C C O C H H H

H H H H C C O C H Methyl Ethyl Ether H H H Naming Ethers Count the amount of carbons on the left side of the Oxygen first. Count the number of carbons on the right side of the oxygen. The carbons on the left make Methyl and the carbons on the right make Ethyl, then put Ether at the end. H H H H C C O C H Methyl Ethyl Ether H H H

H H H O H C C C C H H H H Aldehyde Aldehydes are known when there is one double bonded oxygen atom at the beginning or the end of a carbon chain. H H H O H C C C C H H H H

H H H O H H C C C H C H H H H Forming Aldehydes Start with a carbon chain (butane). Drop off two Hydrogen atoms. Add a double bonded oxygen to the open carbon. H H H O H H C C C H C H H H H

Butanal H H H O H C C C C H H H H Name It! Four Carbons = butane Since all aldehydes end in –al. Drop the –e and add –al to the end. Butanal H H H O H C C C C H H H H

Ketone Ketones can be identified by the oxygen double bonded to a carbon in the middle of a carbon chain. H H O H H C C C H C H H H

Butan one e H H O H H C C C H C H H H Name a Ketone We have a chain of carbons (4=butane) If the double bonded oxygen is found in the middle of a carbon chain then it is a ketone and the –e must be dropped and add –one in its place Butan one e H H O H H C C C H C H H H

H H O H C C C H O H H Organic Acids!!!!!! Contains a double bonded oxygen and an –OH to the last carbon in the chain Called acids because H+ ions are released when dissolved in water Since ions are present when dissolved, an electric current can be conducted through the water Organic acids are electrolytes! H H O H C C C H O H H

Hexan oic Acid e O H H H H H H H C C C C C C H H O H H H H H H Name the acid Form the Acid Start with the carbon chain REMOVE: -e Hexane Drop off the three hydrogen atoms at the end of the chain ADD: -oic Acid Hexan oic Acid e Add a double bonded oxygen atom and an –OH group to the open carbon atom AND THERE YOU HAVE IT!! O H H H H H H H C C C C C C H H O H H H H H H

H H H O H H C C C C O C H H H H H Ester And Esters smell goood!! Esters have two oxygen atoms present One is connected by double bonds to a carbon atom The other is connected by single bonds but to two carbon atoms An ester is formed from the reaction of an acid and an alcohol. H H H O H H C C C C O C H H H H H

Meth yl Butan oate H H H O H H C C C C O C H H H H H -count the number of carbons on the side that is only touching one carbon. Title it! -Add –yl as the suffix. Meth yl Butan oate -Now count the number of carbons in the chain attached to the two oxygen atoms. -All that’s left if to add –oate to the end H H H O H H C C C C O C H H H H H

N H H H H H H C C C C N H H H H H Amine Amines contain a nitrogen atom the nitrogen atom is found at the end of a carbon chain; attached to one carbon as well as two hydrogen. H H H H H H C C C C N H H H H H

Naming the Amine is easy There are only two steps involved! Count the hydrocarbons Drop the –e and add –amine Butan amine e H H H H H H C C C C N H H H H H

H H H O H H C C C C N H H H H Amide Amides also contains a Nitrogen atom but attached to the same carbon is a double bonded oxygen. H H H O H H C C C C N H H H H

Butan amide e H H H O H H C C C C N H H H H How do I name it?? Amides are just the same as naming the amines except instead of adding –amine, you are adding –amide. Butan amide e H H H O H H C C C C N H H H H

Amino Acids

H H H O H C C C C H O H H N H H Amino Acids… Contains both an amine and an organic acid Organic Acid H H H O H C C C C H O H H N H H Amine

Where are the Amino Acids?? It Must Be Memorized!!! Hmmmm……. Where are the Amino Acids??

NOTE: All the example on how the groups are named are shown on table R in the far right column. Note: The formulas on how each group is drawn is shown in the formula column.

Organic Reactions

Substitution Replacement of one kind of an atom/ group by another kind of atom/group Only happens in Alkanes Alkane + halogen(X2) halocarbon + HX(g) + F2 + HF F

Addition + F2 F F Adding one or more atoms at a double/ triple bond H Only happens in Alkenes/Alkynes + F2 F F H H

Fermentation C6H12O6 -------------> 2 C2H5OH + 2 CO2 Zymase (enzyme) Glucose Ethanol Carbon Dioxide

Esterification Acid and alcohol produce ester and water Fats are Esters dervied from glycerol (a trihydroxy alcohol- has 3 OH groups) and long fatty acids

Glycerol Fats are Esters derived from glycerol (a trihydroxy alcohol- has 3 OH groups) and long fatty acids

Fat + Strong Base Soap + Glycerol Saponification (hydrolysis) Ester breaks up into Acid and Alcohol (reverse of esterification) Produces soap Fat + Strong Base Soap + Glycerol

Combustion Organic (hydrocarbon) + O2 CO2 +H20 Burning (reaction with oxygen) Hydrocarbons burn to form carbon dioxide and water Organic (hydrocarbon) + O2 CO2 +H20 heat In a limited supply of oxygen, C and CO are formed Test to show if there is Carbon Dioxide: Limewater (colorless) turns a milky white color with Carbon dioxide

Polymerization Small molecules join together to form bigger molecules (monomers to polymer) amino acid + amino acid + amino acid protein monomer + monomer + monomer polymer

Polymerization Continued 2 Types: (the words condensation and addition are not on the regents but you must know the ideas about polymerization) Condensation Polymerization: Dehydration synthesis Make water and polymer Natural Protein (DNA) Starch cellulose Artificial Nylon Polyester silicone

n n Addition Polymerization Monomers join together by breaking a double/triple bond n n number of ethene join together number of polyethylene

Finding missing reactants and products in Organic Reactions # of atoms on the left side of the arrow must equal # on the right After the elements/compounds are correctly written, change the coefficient Ex: C2H6 + Cl2 C2H5Cl + ______ HCl

Practice Regents Questions Go online to regentsprep.org! http://regentsprep.org/Regents/core/questions/questions.cfm?Course=CHEM&TopicCode=06

http://www.chemguide.co.uk/basicorg/conventions http://www.chemguide.co.uk/basicorg/conventions/names.html#top/draw.html#top http://www.chemguide.co.uk/basicorg/conventions/names2.html#top http://www.chemguide.co.uk/orgpropsmenu.html#top http://www.chalkbored.com/lessons/chemistry-11/unit-5-answers-handout.pdf http://www.chalkbored.com/lessons/chemistry-11/hydrocarbon-nomenclature-handout.pdf

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