Organic Chemistry Topic 11 Hw P 197 Q

Organic Chemistry Topic 11 Hw P 197 Q 1 to 18 The study of Carbon and its compounds

ORGANIC CHEMISTRY • The study of compounds containing Carbon atoms. • Carbon has 4 valence electrons, always draw it with 4 covalent bonds around it. • When it forms all single bonds the shape of around the carbon is TETRAHEDRAL.

Properties • Solubility – Most nonpolar (like dissolves like) – Most compounds are insoluble in water – Soluble in non-polar solvents O H O

Properties • Most are non-electrolytes – Covalent, no conductivity – (an exception is organic acids)

Properties • Low Melting/ Boiling Points

Properties • Rate of Reaction – Slower than inorganic compounds – High activation energy

Properties • 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

HYDROCARBONS • • • Compounds containing only C and H. 3 open chain families ALKANES ALKENES ALKYNES

Homologous Series or families Group of related compounds in which each member differs from the next by one carbon and 2 hydrogens

Alkanes • Single-bonded hydrocarbons • Hydrocarbon= only carbon and hydrogen atoms • IUPAC name Molecular Formula Generic Formula methane CH 4 ethane C 2 H 6 propane C 3 H 8 As the molecular size and dispersion forces butane C 4 H 10 pentane C 5 H 12 increase, the boiling point and freezing point hexane C 6 H 14 Cn. H 2 n+2 increase heptane C 7 H 16 octane C 8 H 18 nonane C 9 H 20 decane C 10 H 22

Table Q

Alkenes • have one Double-bonded hydrocarbon • Unsaturated • Same prefix as alkanes, with suffix -ene Dien e doub s contai n alke le bonds TWO nes! , and are not

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

Saturated vs Unsaturated compounds Single Bonds Double/Triple Bonds

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

May 30 • How to draw and name different organic compounds? • ISOMERS • HW : RB PG 198 Q 19 TO 33

Isomers Although these structures look • Compounds with: different, they both have the same • the same molecular formulas molecular formula of C • different structural formulas 4 H 10 C 4 H 10 Normal Butane 2 -Methyl Propane

ISOMERS • Same molecular formula but different structural formula. Have different chemical and physical properties.

Alkyl Groups • Have 1 less hydrogen (H) than the corresponding alkane • Ex: • Methyl CH 3 – 1 less H than CH 4 • Ethyl C 2 H 5 – 1 less H than C 2 H 6 32 - pentane Propane

Rules for naming organic compounds For Straight or continuous chains: normal form n -alkanes. For branched compounds: 1. Find the longest continuous chain and name the compound. Branches are alkyl groups and end with –yl. 2. The location of the alkyl group is determined by assigning numbers to the carbon atoms of the longest chain, beginning at the end that will give the lowest number to the carbon that contains the alkyl or special group.

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

Draw Hexane Condensed Formula: Hexane CH 3 -CH 2 -CH 2 -CH 3 st 1 -ane = only single bonds CCCCCC Task:

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

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

Draw: 2, 3 -dimethylbutane

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

May 31 • Objective : Functional groups. • How to distinguish them and what do they do to an organic compound? • Table R • HW P 204 Q 34 TO 48

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

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 Double Bond

Naming Halocarbons • Every halogen has its own prefix to put at the beginning of its name 1, 2 -Di Fluoro propane – It is listed in Table R • When the bonds brake; the halogens fill the empty space 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- O

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! O Ethanol

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. O

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. O Methyl Ether

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

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

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

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

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 Butaneone O

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! O O

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

ters s E And ll sme !! d gooo Ester • 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 an alcohol. O O

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

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

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

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

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

Amino Acids

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

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.

June 1 • • OBJECTIVE: ORGANIC REACTIONS P 208 q 49 to 61 TAKE HOME TEST P 210 ANSWERS IN SCANTRON Q 1 TO 30

Organic Reactions

1. Combustion TABLE I the first 6 rx are combustions • Burning (reaction with oxygen) • Hydrocarbons burn to form carbon dioxide and water heat Organic (hydrocarbon) + O 2 CO 2 +H 20 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

2. Substitution • Replacement of one or more hydrogens in a saturated hydrocarbon by an halogen. Alkane + halogen(X 2) halocarbon + HX(g) + F 2 F + HF

3. Addition • Adding one or more atoms at a double/ triple bond. Could be Hydrogenation (add H) Or Halogenation (add halogens) For alkenes and alkynes! + F 2 H H F F

4. 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

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

6. Fermentation Zymase (enzyme) C 6 H 12 O 6 -------> 2 C 2 H 5 OH + 2 CO 2 Glucose Ethanol Carbon Dioxide

7 POLYMERIZATION • Polymers are made of chains of smaller units called MONOMERS • NATURAL POLYMERS • Protein, starches, cellulose • SYNTHETIC POLYMERS • Nylon, rayon, polyethylene

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

Polymerization • 2 Types: • Condensation Polymerization: – Dehydration synthesis, occur when water is remove from primary alcohols. Have ether or ether linkages. – Make water and polymer Natural • Protein (DNA) • Starch • cellulose Artificial • Nylon • Polyester • silicone

• 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: • C 2 H 6 + Cl 2 C 2 H 5 Cl + ______ HCl

Practice Regents Questions • Go online to regentsprep. org! • http: //regentsprep. org/Regents/core/questio ns/questions. cfm? Course=CHEM&Topic. Code= 06

• http: //www. chemguide. co. uk/basicorg/conventions/n ames. html#top/draw. html#top • http: //www. chemguide. co. uk/basicorg/conventions/n ames 2. 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

• http: //reviewgamezone. com/game. php? id=66 9 • http: //www. youtube. com/watch? v=1 q. GPWd m 2 Ml. I