Carbon Bonding Isomers Naming Reference Tables Functional Groups. Reactions

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1 arbon Bonding Isomers Naming Reference Tables Functional Groups 2 Reactions Not electrolytes; they do not generally conduct electricity. Low melting points; they are nonpolar with weak forces of attraction. Organic reactions are generally slower than inorganic (ionic) reactions. arbon forms four covalent bonds in the shape of a tetrahedron

2 Saturated hydrocarbons Alkanes Only single bonds between carbons Name ends in ane General formula n 2n+2 Methane 4 Ethane 2 6 Unsaturated hydrocarbons ontain at least one double or triple bond Alkenes ontain one double bond Name ends in ene General formula n 2n Alkynes ontain one triple bond Name ends in yne General formula n 2n Alkanes Alkenes Alkynes Aromatics 10 Which element has atoms that can form single, double, and triple covalent bonds with other atoms of the same element? (1) hydrogen (2) oxygen (3) fluorine (4) carbon

3 Number of arbons Prefix Meth Eth Prop But Pent Alkane n 2n+2 Methane 4 Ethane 2 6 Propane 3 8 Butane 4 10 Pentane 5 12 Example Alkene n 2n Ethene 2 4 Propene 3 6 Butene 4 8 Pentene 5 10 Alkyne n 2n-2 Ethyne 2 2 Propyne 3 4 Butyne 4 6 Pentyne Which hydrocarbon is saturated? (1) propene (2) ethyne (3) butene (4) heptane Alkanes are saturated hydrocarbons. 15 Methane Ethane Each line represents a covalent bond - a shared pair of electrons. 16 propene The double bonds makes this hydrocarbon an alkene ethyne The triple bonds makes this hydrocarbon an alkyne

4 The empirical formula of a compound is 2 Which molecular formula is correctly paired with a structural formula for this compound? A carbon group connected to a chain is called an alkyl group. To name the alkyl group, use the prefix for the number of carbons and add yl. - 3 Methyl Ethyl 20 ydrogen always has 1 bond Oxygen always has 2 bonds Nitrogen always has 3 bonds or or Which structural formula is incorrect? arbon always has four bonds. O or O N Nonpolar onlyvan der Waals forces Larger molecular weight Stronger forces Name Number of arbon Atoms Molecular Formula Melting Point, o Boiling Point, o # of Isomers ompound Methane Ethane Propane Butane Pentane Formula MW Linear Alkanes: 1-4 atoms: gas at room temp 5-15 atoms: liquid at room temp >15 atoms: solid at room temp Boiling point ( ) Methane Ethane Propane Butane Pentane exane eptane Octane Nonane Decane

5 Find the longest continuous chain of carbons. This is the backbone. Find the name of the backbone. Find the name of the alkyl group (or groups) attached to the backbone. Name the alkyl group and then the name of the backbone. Use a number to indicate which carbon the alkyl group is attached to if necessary. 25 # of atoms Alkane Methane Ethane Propane Butane Pentane exane eptane Octane Nonane Decane Alkyl substituents Methyl Ethyl Propyl etc. Root: number of atoms Suffix: functional group (-ane for alkanes) (-yl for alkyl groups) Find the longest chain 3- methyl hexane Find the alkyl group ounting from each direction find the carbon where the alkyl group is attached (the lower number) 27 3-methylhexane 28 Use a prefix cyclo when a ring is formed To make a ring, two ydrogen atoms are removed yclopentane is a 5 carbon ring with all single bonds. Benzene ( 6 6) drawn 3 different ways. Every other carbon bond is a double-bond. 29 5

6 32 Structure controls Function Each functional group has predictable reactivity 34 Reference Table R ont d. Examples of esters

7 Production and naming of esters in lab Given the formulas of four organic compounds: Which pair below contains an alcohol and an acid? (1) a and b (3) b and d (2) a and c (4) c and d alocarbons (or halides) have a halogen (F, l, Br, I) in place of a hydrogen Name the halogen first (fluoro, chloro, bromo, iodo) then name the alkane If there are more than 2 carbons in the chain, use a number to indicate which carbon the X group is attached to. (Number from the direction that gives the smallest number) Alcohols have the hydroxyl group -O The prefix is the number of carbons in the longest chain Name the alkane and drop the letter e The suffix is -ol If there are more than 2 carbons in the chain, use a number to indicate which carbon the O group is attached to. (Number from the direction that gives the smallest number) 1-chloropropane 2-bromobutane 1-propanol 2-propanol l Br O O

8 Which compound is an alcohol? (1) propanal (2) ethyne (3) butane (4) methanol Ethers have an Oxygen in the chain of carbons Name the alkyl groups on either side of the O that is in the chain If both alkyl groups are the same it is named once with the prefix DI in front of it. Methyl ethyl ether Dimethyl ether O O Aldehydes have a double bonded Oxygen on the last carbon in the chain. Name the alkane, drop the e and add al Ketones have a double bonded Oxygen on a carbon in the middle of the chain. (Not the last carbon) Name the alkane, drop the e and add one If there are more than 4 carbons in the chain, use a number to indicate the location of the =O propanal methanal O O butanone O 3-pentanone O Acids have a double bonded Oxygen and an O on the last carbon in the chain. Name the acid, drop the e and add oic acid This is O and not O the arbon is bonded to the O Amines have a nitrogen bonded to the carbon chain. The nitrogen may have two, one or no hydrogen atoms bonded to it. Name the alkane, drop the e and add amine If there are more than two carbon atoms, use a number to indicate which carbon the N is attached to. Propanoic acid Pentanoic acid ethanamine 2-Pentanamine O O N 2 O O N

9 O O Ethanoic acid O Ethanal N 1-Propanamine 2-butene Which compound is classified as a hydrocarbon? (1) Ethane (2) Ethanol (3) chloroethane (4) ethanoic acid O 3-hexanone O 2-pentanol Which pair of compounds are alcohols? Which type of organic compound is represented by the structural formula shown below? (1) aldehyde (2) alcohol (3) ether (4) ester The fat dog shook himself, and then rolled over on the wet rug. OR Pentane 5 12 Methylbutane The dog shook the fat rug, then rolled over and wet on himself. These two statements use the same words... but have very different meanings! Likewise, isomers may have the same formula, but have very different structures 9

10 1-butanol ( 4 9 O) diethyl ether ( 2 5 O 2 5 ) 4 arbon, 10 ydrogen, 1 Oxygen propanal ( 2 5 O) 2-propanone ( 3 O 3 ) 2-methylpropane or 3 arbon, 6 ydrogen, 1 Oxygen Isomers have the same chemical formulas but different structural formulas. 56 Which compound is an isomer of pentane? (1) butane (2) propane (3) methyl butane (4) methyl propane Which formula is an isomer of butane? Given the structural formula for butane: Draw the structural formula for an isomer of butane

11 Which compound has an isomer? Alkenes have one double bond Ethene 2 4 Alkynes have one triple bond 61 Ethyne In saturated hydrocarbons, carbon atoms are bonded to each other by Alkenes and Alkynes are unsaturated. By breaking the multiple bond in alkenes and alkynes, more hydrogen atoms can be added Alkanes are saturated. (1) single covalent bonds, only (2) double covalent bonds, only (3) alternating single and double covalent bonds (4) alternating double and triple covalent bonds Alkanes do not have multiple bonds, therefore, they already have as many hydrogen atoms as they could possibly hold Addition 2, l 2, Br 2, l, Br is added to an unsaturated hyrdrocarbon. Both atoms are added to where the double (or triple) bond was located. Key to look for Unsaturated hydrocarbon reactant and one product. l l + l

12 Addition of hydrogen 2 an be used to saturate and unsaturated hydrocarbon. It uses a catalyst such as platinum (Pt) + 2 Pt Which formula correctly represents the product of an addition reaction between ethene and chlorine? (1) 2 l 2 (2) 3 l (3) 2 4 l 2 (4) 2 3 l Substitution A halogen is reacted with a saturated hydrocarbon. One of the halogen atoms substitutes one of the hydrogen atoms. Key to look for Saturated hydrocarbon reactant and two product. Polymerization joining many small molecules together to form a large molecule A single unit is called a monomer Many monomers are bonded together to form a polymer Polymers can be natural or artificial l + l UV 2 + l 69 Natural Polymers Protein Rubber ellulose Artificial Polymers Polyester Nylon Styrofoam 70 The process of joining many small molecules into larger molecules is called (1) neutralization Which type of reaction is represented by the equation below? Note: n and n are very large numbers equal to about (2) polymerization (3) Saponification (4) substitution (1) Esterification (3) saponification (2) fermentation (4) polymerization

13 Esterification making an ester by combining an alcohol with an organic acid O O + O O O + 2 O 73 Esters have a double bonded Oxygen and an O bonded to another carbon. Name the alkyl group that came from the alcohol. Name the acid but drop ic acid and replace it with ate. Propanoic acid + pentanol Propanoic acid O O Pentyl propanoate + water 1-Pentanol O 74 Propanoic acid 1-Pentanol O O O Pentyl propanoate Methyl ethanoate Ethanoate O O Acid Determine which side was the alcohol and which side was the acid by drawing a line through the oxygen in the chain. The side with the double bonded O was the acid. Alcohol Methyl Alcohol will make you yl if you ate the acid Given the ester: ethyl butanoate a. Draw the structural formula for this ester. b. Determine the gram formula mass of this ester. O 6 x 12 = 72 O O 2 x 16 = 32 O N O N 12 x 1 = g Even if you got the structure wrong but you got the correct mass for the structure you drew, you got one point. 77 From ammonia (N 3 ) From amine ( 3 N 2 ) 78 13

14 Amides have a double bonded Oxygen and a Nitrogen. Name the alkyl group that came from the amine. Name the acid but drop oic acid and replace it with amide. Propanoic acid + 1-pentanamine Propanoic acid O O Pentyl propanamide + water 1-Pentanamine 2 N 79 Propanoic acid O O 1-Pentanamine N Pentyl propanamide 80 An amino acid is a compound that has an amine group on one side and an acid group on the other. O O R N O O R N O R N Remove water O R O N R is the only part that changes in different amino acids Fermentation yeast and bacteria can make ethanol and carbon dioxide by breaking down sugar using an enzyme. The alcohol can be used to make beer and wine, The carbon dioxide can be used to make bread rise or make the bubbles in beer and champagne. Enzyme 6 12 O O + 2O 2 Saponification is a reaction in which a lipid (fat or oil) is used to make soap

15 ombustion Burning ombining with oxygen to produce carbon dioxide and water In which reaction is soap a product? (1) addition (2) substitution (3) Saponification Burning Methane 4 + 2O 2 O O (4) polymerization Burning Octane O 2 16O O Burning Ehtanol 2 5 O + 3O 2 2O O ) ydration addition of water to an alkene 2) Addition addition to alkene (double) or alkyne (triple-bond) 3) ydrogenation addition of ; product will be an alkane (saturated ) 4) Dehydrogentation remove ; product will be an alkene or alkyne (unsat. ) 5) Esterification form an ester from organic acid (-OO) and alcohol (-O) 6) Soaponification form a soap Glycerol + Fatty Acid Soap + 20 Trihydroxyl 7) Fermentation yeast breaksdown glucose Glucose Alcohol + arbon Dioxide 6 12O O + 2 O 2 8) Polymerization form a polymer Addition Polymer add monomers together get polymer n 2 4 ( 2 4)n ondensation Polymer remove water; get polymer