Chemistry 11 Hydrocarbon Alkane Notes. In this unit, we will be primarily focusing on the chemistry of carbon compounds, also known as.

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1 1 Chemistry 11 Hydrocarbon Alkane Notes In this unit, we will be primarily focusing on the chemistry of carbon compounds, also known as. Why is organic chemistry so important? Many of the compounds that surround us in everyday life are made up of organic compounds. Some are found naturally, while others are produced synthetically. Some examples include: C 8 H 18 CH 4 C 17 H 21 NO 4 C 10 H 14 N 2 C 6 H 12 O 6 What are organic compounds primarily made of? As you can see from the examples above, organic compounds of mostly made of two types atoms. They are and! Hydrocarbon: Before we go any further, we must become familiar with Carbon! Carbon has electrons in its outer shell, so it can form (and only ) bonds with other elements. Hydrogen atoms usually attach to the carbons. Each carbon atom when singly-bonded has a geometry C C Tetrahedral Geometry Simplified Drawing Geometry

2 2 Carbon atoms can form bonds with other carbon atoms! The end result is a chain of carbons known as a. C C C C C C C C (carbon atom) (carbon backbone) A lkanes The simplest type of hydrocarbon Alkanes: They follow the general formula (eg. C 2 H 6 ) All the bonds follow a arrangement, all the bonds form angles with each other, and are in length They are very as C C, and C H bonds are strong and hard to break Short C 1 to C 4 chains are, C 5 to C 15 chains are, and long chains such as C 16 and above are known as. Writing the structure and formula for hydrocarbons There are 3 ways to represent a hydrocarbon formula For example, propane (C 3 H 8 ): Full structure: Condensed structure: Molecular Formula: Note: Since each carbon atom is bonded to the maximum number of hydrogens available, they are known as Hydrocarbons!

3 3 Naming Unbranched (Straight-Chained) Alkanes Rules: 1. Count the number of carbon atoms in the carbon backbone. Use a prefix to denote the number of carbons. Number of Carbons Prefix Used Number of Carbons Prefix Used Add the ending to the prefix. CH 4 carbon atom = C 5 H 12 carbon atoms = N aming Side Chains Some hydrocarbon chains can have a side chain (or side group). These groups are known as groups. CH 3 CH 2 CH CH 2 CH 2 CH 3 CH2 CH 3 Alkyl Group: To name an alkyl group, use the for the number of carbon atoms and add the ending Eg. CH 4 CH 3 (one H removed = )

4 4 Naming Branched Alkanes Rules: 1. Identify the longest continuous chain of carbon atoms. This is the! 2. Identify all the side chains that branch off from the parent chain. 3. Number the carbon atoms on the parent chain consecutively starting from either the left side or the right side that gives the lowest possible set of numbers to the side chains 4. Starting with the first side chain in alphabetical order, name the carbon number the alkyl group is attached to, followed by a dash, and then the name of the alkyl group (eg. 2-methyl) 5. If you have more than one of the same alkyl group, list each carbon number where the repeated group is attached, separated by commas, with a dash, and add the prefix to the alkyl group to show how many identical groups are attached. (eg. 2,3-dimethyl) The prefixes that you use are the following: Number of times repeated Prefix Number of times repeated Prefix Name the parent hydrocarbon chain last CH 3 CH CH 2 CH 2 CH 3 parent chain = CH3 side chain on Carbon CH 3 CH CH 2 CH CH 2 CH 2 CH 2 CH 3 CH3 CH 2 CH 3

5 5 CH 2 CH 3 CH 3 CH 2 CH 2 CH CH CH CH 3 CH 3 CH 2 CH2 CH 3 S tructural Isomers Now that you know both branched and unbranched hydrocarbons exist, you will need to consider these types of structures when given a molecular formula. Consider the following formula: C 4 H 10 The structure of this alkane can have the following possibilities: or Straight-chained Branched Both of these structures have the same formula and are called Structural Isomers: C ycloalkanes Cyclic Hydrocarbons Hydrocarbons don t necessarily have to be in chains. They also exist in cyclic (ring) forms! These types of hydrocarbons are known as. Cycloalkanes have a general formula of We will primarily be dealing with 5 types of cycloalkanes: Cyclopropane = C 3 H 6 Cyclobutane = C 4 H 8 Cyclopentane = C 5 H 10

6 6 Cyclohexane = C 6 H 12 Cyclooctane = C 8 H 16 Naming Substituted Cycloalkanes Substitued cycloalkanes follow the same naming rule as branched alkanes except: 1. A single substituent does not require a number to indicate the position of attachment. All carbons are considered identical. 2. If more than one substituent is present, the first substituent is assumed to be at carbon 1, and the remaining substituents are numbered either clockwise or anticlockwise to have the lowest set of overall number values. A lkyl Halides Halogen Side Groups Hydrocarbons can have halogens as side chains. These compounds are known as. The halogens found are,,, and. Alkyl halides have different reactivities depending on the type of halogen found. Compounds with atoms tend to be the least reactive like Teflon, while compounds with atoms tend to be the most reactive.

7 7 Most Reactive: I > Cl or Br > F Least Reactive: Namin g Alkyl Halides These compounds follow the same rules as branched alkanes except: The halo groups F, Cl, Br, and I are named as fluoro, chloro, bromo, and iodo respectively. CH 3 CH CH 3 F Br I CH 3 CH CH CH CH 2 CH 3 CH 3

8 Chemistry 11 Alkenes and Alkynes Notes As you now know, alkanes are known as saturated hydrocarbons because they contain singlebonded carbon atoms with the maximum number of hydrogens. However, there are hydrocarbons that contain multiple-bonded carbon atoms. These are known as hydrocarbons because they have less hydrogen atoms when compared to equivalent alkanes. We will investigate two types in this section: and. Alkenes Double-Bonded Carbon Atoms Alkenes: Double bonds can be found at the or in the of the carbon chain Alkene structure can be represented in two ways: or Naming Alkenes Rules: The rules are similar to the Branched Alkanes except for the following: 1. Identify the longest continuous carbon chain that contains the double bond. 2. Change the ending for the parent chain to 3. Number the parent chain so that the double bond gets the lowest possible number. 4. Use a number followed by a dash in front of the name of the parent chain to indicate which carbon the double bond is bonded to. (eg. 2-butene) CH 2 = CH CH 2 CH 3

9 CH 2 = C CH 2 CH 3 CH 3 Geometric Isomers in Alkenes The Cis / Trans Thing When we were looking at alkanes, we found out that all the carbons were single-bonded. This would allow for lots of flexibility in the bond and free rotation around each bond. The arrows show the free rotation around the carbon atoms in propane. However, if we look at alkenes, they contain a double bond in the carbon backbone. What does that do to the geometry of those carbon atoms directly affected by the double bond?

10 The tetrahedral shape of the carbon atom now becomes! The bond angle between the three atoms attached to the double-bonded carbon is The double bond provides more strength to the molecule. It the affected carbon atoms from around the double bond. The rigid structure of alkene carbons has an important consequence:! Two requirements for isomers are: 1. A double bond 2. Groups (other than hydrogen atoms) which are attached to each of the carbons involved in the double bond. 2-butene has two isomers possible H 3 C CH 3 H 3 C H \ / \ / C = C C = C / \ / \ H H H CH 3 The two methyl groups are on the same side of the double bond. The two methyl groups are on opposite sides of the double bond. Alkynes Triple-Bonded Carbon Atoms Alkynes: Triple bonds can be found at the or in the of the carbon chain Alkyne structure can be represented in two ways: or

11 Naming Alkynes Rules: The rules are similar to the Alkenes except for the following: 1. Identify the longest continuous carbon chain that contains the triple bond. 2. Change the ending for the parent chain to CH 3 C C CH 3 Geometry of Alkynes HC C CH 2 CH CH 3 CH 3 Alkynes contain a triple bond in the carbon backbone which is very rigid. It causes the carbons affected to be locked to each other forming straight-line structures. The tetrahedral shape of the carbon atom now becomes! The bond angle between the two atoms attached to the triple-bonded carbon is The triple bond provides super strength to the molecule. It the affected carbon atoms and them from around the triple bond.

12 1 Chemistry 11 Aromatic Compounds Study Guide We have witnessed the existence of cyclic hydrocarbons in alkanes in the previous section. Is it also possible to have cyclic hydrocarbons for alkenes? The answer is absolutely! As you know, the carbons affected by the double bond will have its geometry altered. This would put a in the ring structure causing some or in the cyclic hydrocarbon. Therefore, cycloalkenes are structures than cycloalkanes. Structure of Cyclohexane Structure of Cyclohexene However, there is one particular cyclohexene that is really stable. This ring structure, called, has not one but present. The three double bonds are found with the 3 single bonds in the structure. This unusual arrangement provides because the molecule undergoes, where the double bonds can swap places with the single bonds continuously. Resonance Structures of Benzene

13 2 Since benzene molecules can exist in different resonance structures at any given time, benzene is frequently represented as follows: The accurate representation of Benzene The simplified representation in structural diagrams Many large organic molecules actually contain one or more of these benzene rings. These molecules are known as. Aromatic Molecule: The following are some common examples of aromatic molecules: Naphthalene (C 10 H 8 ) Benzo[a]pyrene (C 20 H 12 )

14 3 Naming Substituted Benzenes Substituted Benzenes generally follow the same naming rules as.

15 1 Chemistry 11 Functional Groups Notes So far we have investigated hydrocarbon alkanes and have found that this particular group has limited uses and properties. If all organic molecules were alkanes, then organic chemistry would be useless and boring! Luckily, are found on organic molecules, which give the molecules more and with other compounds. These groups of atoms are known as. Functional Group: Functional groups may allow a molecule to: So far we have seen a couple of examples of functional groups present on hydrocarbons. They are the carbon-carbon double bonds, carbon-carbon triple bonds, and halides. We will now look at other important functional groups that are present in many everyday organic chemicals. General Naming for Hydrocarbons Containing Functional Groups The following molecules containing functional groups will be named according to these general rules: 1. Find the longest carbon chain containing the functional group. This chain determines the parent name of the compound. 2. Change the ending of the parent name to the ending specific to the functional group. 3. Number the parent chain from the end nearest to the functional group so that the functional group gets the lowest possible number. Place this number, along with a dash in front of the parent name. 4. Identify the side chains, determine the carbon number that they are attached to, and name them in alphabetical order.

16 2 Alcohols Alcohol: They have a general formula of C n H 2n+1 OH Properties of Alcohols High boiling and melting points (due to the H from one OH group interacts with the O from another OH group) All alcohols are poisonous, yes even ethanol! They are solvents (they have a specific positively charged end and a negatively charged end) Alcohols have two opposing solubility tendencies due to their structure: Naming Alcohols The group tends to with water (which is also a polar molecule) making the alcohol The tends to make alcohols in water Therefore, short-chained alcohols tend to be more in water such as methanol, ethanol, propanol, and butanol, while longer chains such as pentanol and higher are. Use an ending of for the parent chain when naming alcohols CH 3 CH CH 2 CH 3 OH CH 3 CH CH 2 CH CH 2 CH 3 CH 3 OH

17 3 Carboxylic Acids Carboxylic Acid: The COOH group maybe shown as the following: They have a general formula of C n H 2n+1 COOH Properties of Carboxylic Acids High boiling and melting points due to hydrogen bonding They are polar molecules Can act as (usually referred to as ) Naming Carboxylic Acids Use an ending of for the parent chain when naming carboxylic acids (Note: the carbon in the COOH group is included in the parent chain!) CH 3 COOH (commonly called Acetic Acid found in vinegar!) CH 3 CH 2 CH 2 COOH (the smell from smelly feet!)

18 4 Esters Ester: The COO group maybe shown as the following: They have a general formula of C n H 2n+2 COO Properties of Esters They are good solvents (eg. Used in nail polish remover) Used to make (long-chained molecules); found in fats, oils, and waxes Pleasant smelling; often used in foods and other fragrances Ester Odour Ester Odour Ethyl butanoate Pentyl propanoate Pentyl ethanoate Ethyl methanoate Octyl ethanoate Methyl butanoate Naming Esters (Note the following exceptions:) Use an ending of for the parent chain when naming esters (Note: You can omit the position of the COO group in the naming of the parent chain) The hydrocarbon chain attached to the of the COO group is called the. The carbon in the COO group is also part of the parent chain! The hydrocarbon chain attached to the of the COO group is named as an. The name of this alkyl group exists as a from the parent chain. CH 3 CH 2 COO CH 2 CH

19 5 Preparations of Esters CH 3 COO CH 2 CH 2 CH Esters are made by reacting a with an in the presence of an such as HCl or H 2 SO 4. This process is known as an reaction. The following is an example of preparing methyl ethanoate from ethanoic acid and methanol: catalyst Ethanoic acid Methanol Methyl ethanoate Water O O H + CH 3 C O H + HO CH 3 CH 3 C O CH 3 + H 2 O The H from the acid and the OH from the alcohol are removed to form H 2 O. Ethanoic acid loses an H to become ethanoate in the ester. Methanol loses OH, to become a methyl group in the ester. Try to name the products and draw the esterification reaction for each test tube in Lab 23B. Aldehydes Aldehyde: The CHO group maybe shown as the following: They have a general formula of C n H 2n O

20 6 Properties of Aldehydes Generally soluble in water due to hydrogen bonding Common aldehydes are liquids Distinctive odours (generally pleasant!) Naming Aldehydes Use an ending of for the parent chain when naming aldehydes (Note: the carbon in the CHO group is included in the parent chain!) Since the CHO group is found on the of a hydrocarbon chain, the of the CHO group can be from the parent chain name. O H C H (commonly called Formaldehyde Used as a preservative in biological specimens) O CH 3 CH 2 CH C H CH 3

21 7 Amides Amide: The CONH 2 group maybe shown as the following: They have a general formula of C n H 2n+1 CONH 2 Properties of Amides Polar molecules and good solvents The amide group forms the backbone of all protein molecules (links individual amino acid subunits together) Can be used to form synthetic polymers Naming Amides Use an ending of for the parent chain when naming amides (Note: the carbon in the CONH 2 group is included in the parent chain!) Since the CONH 2 group is found on the end of a hydrocarbon chain, the position of the CONH 2 group can be omitted from the parent chain name. CH 3 CONH 2 O CH 3 CH CH 2 C NH 2 CH 3

22 8 Ketones Ketone: The CO group maybe shown as the following: They have a general formula of C n H 2n O (same as aldehydes) Properties of Ketones Similar properties as Aldehydes Naming Ketones Use an ending of for the parent chain when naming ketones (Note: the carbon in the CO group is included in the parent chain!) O CH 3 C CH 3 (known as Acetone common ingredient in nail polish remover) O CH 3 C CH 2 CH CH 3 CH 3

23 9 Amines Amine: They have a general formula of C n H 2n+1 NH 2 Properties of Amines They are and react with acids Smelly compounds (tend to have a fish-like odour) Naming Amines Use an ending of for the parent chain when naming amines CH 3 CH 2 CH 2 NH 2 CH 3 CH CH 2 CH 2 NH 2 CH 3 Ethers Ether: The oxygen atom maybe shown as the following: They have a general formula of C n H 2n+2 O

24 10 Properties of Ethers Tend to be quite molecules Good solvents Some ethers (eg. Diethyl ether) are used as an in hospitals on people and by biologists on animals and insects Naming Ethers (Note the following exceptions:) Consider the atom in the ether group to be the and use the name Treat the hydrocarbon chains attached to the oxygen atom as and name them in alphabetical order with in between each side chain. CH 3 O CH 2 CH 3 CH 3 O CH 3 In Organic Chemistry, you will come across molecules that contain more than one type of functional groups. In that case, you will have to determine which functional group has the highest priority in naming by using a functional groups naming chart. You will not be expected to do this in Chemistry 11 but for future reference, the following chart is provided.

25 11 Chemistry 11 Functional Groups Naming Chart Highest Priority Functional Group Carboxylic Acid Ester Amide Aldehyde Ketone Formula O C OH O C O General Equation C n H 2n+1 COOH C n H 2n+2 COO O C NH 2 C n H 2n+1 CONH 2 O C H O C C n H 2n O C n H 2n O Example O CH 3 -CH 2 -C-OH Propanoic acid O CH 3 -CH 2 -C-O-CH 3 Methyl propanoate O CH 3 -CH 2 -C-NH 2 Propanamide O CH 3 -CH 2 -C-H Propanal O CH 3 -CH 2 -C-CH 2 -CH 3 3-pentanone Nomenclature - anoic acid (pos. # not rqd!) - anoate (alkyl group on oxygen atom) - anamide (pos. # not rqd!) - anal (pos. # not rqd!) - anone Lowest Priority Alcohol OH C n H 2n+1 OH CH 3 -CH 2 -CH 2 -OH 1-propanol Amine NH 2 C n H 2n+1 NH 2 CH 3 -CH 2 -CH 2 -NH 2 1-propanamine Ether O C n H 2n+2 O CH 3 -O-CH 2 -CH 3 Ethyl methyl ether Alkene C = C C n H 2n CH 2 =CH-CH 2 -CH 3 1-butene Alkyne C C C n H 2n 2 CHC-CH 2 -CH 3 1-butyne Alkane & C C Alkyl C n H 2n+2 CH 3 -CH 2 -CH 2 -Cl Halides F,Cl,Br,I 1-chloropropane - anol - anamine - ether (alkyl alkyl ether) - ene [cis/trans isomers] - yne - ane

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