GRADE12CHEMISTRY

OLYMPIADSCHOOL

WEDNESDAY2.30 4.30 WEDNESDAY 2 304 30 FRIDAY4.456.45

OrganicChemistry Organic Chemistry

Classifying Organic Compounds

Organic chemistry is the study of compounds that are based on CARBON. Natural gas, rubbing alcohol, aspirin, aspirin and the compounds that give fragrance to a rose, are all organic compounds. In this lesson you will learn how to identify and name lesson, molecules from the basic families of organic compounds. You will be introduced to the shape, structure, and properties of different types of organic compounds.

THECARBONATOM THE CARBON ATOM

Th There are several million organic compounds, b t only l illi i d but l about a quarter of a million inorganic compounds ( (compounds that are not based on carbon). Why are p ) y there so many organic compounds? The answer lies in the bonding properties of carbon. C b atoms can f Carbon t form strong single, t i l double, or triple bonds with other carbon atoms. In a single carbon carbon bond one pair of electrons is carbon-carbon bond, shared between two carbon atoms. In a double bond, two pairs of electrons are shared between two atoms. In p a triple bond, three pairs of electrons are shared between two atoms.

 M l Molecules th t contain only single carbon-carbon b d l that t i l i l b b bonds are saturated. In other words, all carbon atoms are bonded to the maximum number of other atoms: four. No more bonding can occur. Molecules that contain double or triple carbon-carbon bonds are unsaturated. The carbon atoms on either side of the double or triple bond are bonded to less than four atoms each. There is potential for more atoms to bond to each of these carbon atoms. Carbon compounds in which carbon forms only single bonds have a different shape than compounds in which carbon forms double or triple bonds.

Molecular Shape and Polarity

The three dimensional shape of a molecule is three-dimensional particularly important when the molecule contains polar covalent bonds. As you may recall from your previous chemistry course, a polar covalent b d i a covalent h i t l l t bond is l t bond between two atoms with different electronegativities. Electronegativity is a measure of how strongly an atom attracts electrons in a chemical bond. The electrons in a po a covalent bond are a ac ed o e strongly o e polar co a e bo d a e attracted more s o g y to the atom with the higher electronegativity. This atom has a partial negative charge, while the other atom has a partial positive charge. Thus, every polar bond has a bond dipole: a partial negative charge and a partial positive charge, separated by the length of the bond.

 The figure illustrates the polarity of a double carbon carbonoxygen bond. Oxygen has a higher electronegativity than carbon. Therefore, the oxygen atom in a carbon-oxygen bond has b d h a partial negative charge, and th carbon atom ti l ti h d the b t has a partial positive charge.

O h examples of polar covalent b d i l d CO OH Other l f l l bonds include CO, OH, and NH. Carbon and hydrogen attract electrons to almost the same degree. Therefore, when carbon is g bonded to another carbon atom or to a hydrogen atom, the bond is not usually considered to be polar. For p , p example, CC bonds are considered to be non-polar.

OH>

NH>

H2O>

Predicting Molecular Polarity

A molecule i considered t b polar, or t have a l l is id d to be l to h molecular polarity, when the molecule has an overall imbalance of charge. That is, the molecule has a region g , g with a partial positive charge, and a region with a partial negative charge. S Surprisingly, not all molecules with polar b d are polar i i l t ll l l ith l bonds l molecules. For example, a carbon dioxide molecule has two polar CO bonds, bu it is not a po a molecule. O o po a bo ds, but s o polar o ecu e On the other hand, a water molecule has two polar OH bonds, and it is a polar molecule.

 To determine molecular polarity you must consider the polarity, shape of the molecule and the bond dipoles within the molecule. If equal bond dipoles act in opposite directions in threedimensional space, they counteract each other. A molecule with identical polar bonds that point in opposite directions is not polar. p p For example, Carbon dioxide, CO2, has two polar CO bonds acting in opposite directions, so the molecule is non-polar. Carbon tetrachloride, CCl4, has four polar CCl bonds in a tetrahedral shape Therefore carbon shape. Therefore, tetrachloride is also non-polar.

 If the b d di l i a molecule d not th bond dipoles in l l do t counteract each other exactly, the molecule is polar. Two examples are water, H2O, and chloroform, CHCl3. Although each molecule has polar bonds, t e bo d d po es the bond dipoles do not act in e act y ot exactly opposite directions. The bond dipoles do not counteract each other, so these two molecules are polar.

Normallyshown Normall sho n structureof Chloroform VS. Spacefilling Structureof Structure of Chloroform (Noticehowyoucan getasenseforthe polarityofthemolecule inthesecondcase in the second case butnotinthefirst)

Howtopredictifamoleculeispolar How to predict if a molecule is polar

Th steps below summarize h The t b l i how t predict whether or to di t h th not a molecule is polar. The Sample Problem that follows g gives three examples. p Note: For the purpose of predicting molecular polarity, you can assume that CH bonds are non-polar. In fact, they h th have a very l low polarity. l it Step 1 Does the molecule have polar bonds? If your answer is no see below If your answer is yes go to step no, below. yes, 2. If a molecule has no polar bonds, it is non-polar. Examples: CH3CH2CH3 , CH2CH2

Continuation
Step 2 Is there more than one polar bond? If your answer is no, see below. If your answer is yes, go to step 3. If a molecule contains only one polar bond, it is polar. Examples: CH3Cl, CH3CH2CH2Cl Step 3 Do the bond dipoles act in opposite directions and counteract each other? Use your knowledge of threey g dimensional molecular shapes to help you answer this question. If in doubt, use a molecular model to help you visualize the shape of the molecule If a molecule contains molecule. bond dipoles that do not counteract each other, the molecule is polar. Examples: H2O, CHCl3. If the molecule contains dipoles that th t counteract each other, th molecule i nont t h th the l l is polar.Examples: CO2, CCl4

HOMEWORKQUESTIONS1: HOMEWORK QUESTIONS 1:

1. Predict d k t h the three-dimensional shape around 1 P di t and sketch th th di i l h d each single-bonded atom. (a) C and O in CH3OH (b) C in CH4 2. Predict and sketch the three-dimensional shape of each three dimensional multiple-bonded molecule. (a) HCCH (b) H2CO 3. Identify any polar bonds that are present in each molecule i questions 1 and 2 l l in ti d 2.

4. For each molecule in questions 1 and 2, p predict whether the molecule as a whole is polar or non-polar.

HYDROCARBONS:
In this section, we will review the structure and names of hydrocarbons. As you may recall from your previous chemistry studies hydrocarbons are the simplest type studies, of organic compound. Hydrocarbons are composed entirely of carbon and hydrogen atoms, and are widely used as fuels. Gasoline, propane, and natural gas are common examples of hydrocarbons. Because they contain only carbon and hydrogen atoms, hydrocarbons are non-polar compounds. d

Alkanes, Alkenes, Alkanes Alkenes and Alkynes

An alkane is a hydrocarbon that has only single bonds. Alkanes that do not contain rings have the formula CnH2n + 2 An alkane in the shape of a ring is called a 2. cycloalkane. Cycloalkanes have the formula CnH2n. An alkene is a compound that has at least one double bond. p Straight-chain alkenes with one double bond have the same formula as cycloalkanes, CnH2n.

ListofRootsforAlkanes List of Roots for Alkanes

1C=methane 1C th 2C=ethane 3C=propane 3 C propane 4C=butane 5C=pentane 5 C = pentane 6C=hexane 7C=heptane 7 C = heptane 8C=octane 9C nonane 9 C =nonane 10C=decane

 A double bond involves two pairs of electrons. In a double bond, one pair of electrons forms a single bond and the other pair forms an additional, weaker bond The additional bond. electrons in the additional, weaker bond react faster than the electrons in the single bond. Thus, carbon-carbon g , double bonds are more reactive than carbon-carbon single bonds. When an alkene reacts, the reaction almost always occurs at the site of the d bl b d l l h i f h double bond.

FUNCTIONALGROUPS FUNCTIONAL GROUPS

A functional group is a reactive group of bonded atoms that appears in all the members of a chemical family. Each functional group reacts in a characteristic way way. Thus, functional groups help to determine the physical and chemical properties of compounds. p p p For example, the reactive double bond is the functional group for an alkene. In this course, you will encounter many different functional groups.

 An alkyne is a compound that has at least p g y one triple bond. A straight chain alkyne with one triple bond has the formula CnH2n 2 Triple bonds are even more 2. reactive than double bonds. The functional group for an alkyne is the triple bond

General Rules for Naming Organic Compounds

Th I t The International Union of Pure and ti lU i fP d Applied Chemistry (IUPAC) has set standard rules for naming organic compounds. The systematic (or IUPAC) names of alkanes and most other organic compounds follow the same pattern, shown below. PREFIX + ROOT + SUFFIX

The Root: How Long Is the Main Chain?

The root of a compounds name indicates the number of carbon atoms in the main (parent) chain or ring. To determine which root to use, count the carbons in the main use chain, or main ring, of the compound. If the compound is an alkene or alkyne the alkyne, main chain or ring must include the multiple bond.

The Suffix: What Family Does the Compound Belong To?

The suffix indicates the type of compound, according to the functional groups present. As you progress through this chapter you will learn the suffixes for different chapter, chemical families. In your previous chemistry course you learned the course, suffixes -ane for alkanes, -ene for alkenes, and -yne for alkynes. Thus, an alkane composed of six carbon atoms in a chain is called hexane. An alkene with three carbons is called propene.

The Prefix: What Is Attached to the Main Chain?

The prefix indicates the name and location of each branch and functional group on the main carbon chain. Most organic compounds have branches called alkyl branches, groups, attached to the main chain. An alkyl group is obtained by removing one hydrogen atom from an alkane. To name an alkyl group, change the -ane suffix to -yl. For example, CH3 is the alkyl group that is derived from methane, CH4. It is called the methyl group, taken from the root meth-.

How to Name Hydrocarbons

St 1 Fi d the root: Identify th l Step Find th t Id tif the longest chain or ring i t h i i in the hydrocarbon. If the hydrocarbon is an alkene or an alkyne, make sure that you include any multiple bonds in y , y y p the main chain. Remember that the chain does not have to be in a straight line. Count the number of carbon atoms in the main chain to obtain the root. If it is a cyclic root Compound, add the prefix -cyclo- before the root. Step 2 Find the su d e suffix: If the hydrocarbon is a a a e, e yd oca bo s an alkane, use the suffix -ane. Use -ene if the hydrocarbon is an alkene. Use -yne if the hydrocarbon is an alkyne. If more than one double or triple bond is present use the prefix present, di- (2) or tri- (3) before the suffix to indicate the number of multiple bonds.

 Step 3 Give a position number to every carbon atom in the main chain. Start from the end that gives you the lowest possible position number for the double or triple bond, if there is one. If there is no double or triple bond, number the compound so that the branches have the p lowest possible position numbers. Step 4 Find the prefix: Name each branch as an alkyl group, and give it a position number. If more than one branch is present, write the names of the branches in alphabetical order l h b ti l d

 Step 4: Put the position number of any double or triple bonds after the position numbers and names of the branches, branches just before the root This is the prefix Note: root. prefix. Use the carbon atom with the lowest position number to g give the location of a double or triple bond. p Step 5 Put the name together: p e + root + suffix. u e a e oge e prefix oo su

How to Draw Hydrocarbons

St 1 D Step Draw th carbon atoms of the main chain. L the b t f th i h i Leave space after each carbon atom for bonds and hydrogen atoms to be added later. Number the carbon atoms. Step 2 Draw any single, double, or triple bonds between the carbon atoms. Step 3 Add the branches to the appropriate carbon atoms of the main chain. Step 4 Add hydrogen atoms so that each carbon atom forms a total of 4 bonds. Remember that double bonds count as 2 bonds and triple bonds count as 3 bonds. p

Single-Bonded Single Bonded Functional Groups

Both 2-propanol and ethanol contain the g p, ( y y) same functional group, an OH (hydroxyl) group, as shown in the figure. Because ethanol and 2-propanol have the same OH 2 propanol functional group, their behaviour is similar.

 Th general formula f a family of simple The lf l for f il f i l organic compounds is R + functional group. The letter R stands for any alkyl group. (If more than one alkyl group is present, R2 and R3 are also used.) For e a p e, the general formula ROH o example, t e ge e a o u a O refers to any of the following compounds: CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH2CH2CH2OH, etc.

 O Organic compounds are named according i d d di to their functional group. Generally, the suffix of a compounds name indicates the most important functional group in the molecule. For e a p e, t e su o example, the suffix -ene indicates the e e d cates t e presence of a double bond, and the suffix ol indicates the presence of a hydroxyl group.

 F Functional groups are a useful way to classify organic ti l f l t l if i compounds, for two reasons: 1 Compounds with the same functional group often 1. have similar physical properties. In the next two sections, you will learn to recognize various functional groups. You will use f ill functional groups t help you predict th physical ti l to h l di t the h i l properties of compounds. 2 Compounds with the same functional group react 2. chemically in very similar ways. Later, you will learn how compounds with each functional group react.

Compounds With Single-Bonded Functional Groups

Alcohols, alkyl halides, ethers, and amines g p g all have functional groups with single bonds. These compounds have many interesting uses in daily life As you learn life. how to identify and name these compounds, compounds think about how the intermolecular forces between their molecules affect their properties and uses.

Alcohols
An alcohol is an organic compound that g p contains the OH functional group. Depending on the position of the hydroxyl group, group an alcohol can be primary primary, secondary, or tertiary.

How to Name an Alcohol

St 1 L Step Locate the l t th longest chain th t contains an OH t h i that t i group attached to one of the carbon atoms. Name the p parent alkane. Step 2 Replace the -e at the end of the name of the parent alkane with -ol. Step 3 Add a position number before the root of the name to indicate the location of the OH group. (Remember to number the main chain of the hydrocarbon so that the hydroxyl group has the lowest possible position number.) If there is more than one OH group, l leave th -e i the name of the parent alkane, and the in th f th t lk d put the appropriate prefix (di-, tri-, or tetra-) before the suffix -ol. ol.

 Step 4 Name and number any other branches on the main chain. Add the name of these branches to the prefix. Step 5 Put the name together: prefix + root + suffix.

HOMEWORKSET4: HOMEWORK SET 4:

Alkyl Halides
A alkyl halide ( l k An lk l h lid (also known as a h l lk haloalkane) is an )i alkane in which one or more hydrogen atoms have been replaced with halogen atoms, such as F, Cl, Br, or I. The p g , , , , functional group of alkyl halides is RX, where X represents a halogen atom. Alkyl halides are similar in structure, polarity, structure polarity and reactivity to alcohols alcohols. To name an alkyl halide, first name the parent yd oca bo e e prefix uo o , c o o , b o o hydrocarbon. Then use the p e fluoro-, chloro-, bromo, or iodo-, with a position number, to indicate the presence of a fluorine atom, chlorine atom, bromine atom, atom or iodine atom atom..

Practice
20. Draw and name an alkyl halide that has three carbon atoms and one iodine atom. 21. Draw and name a second, different alkyl halide that matches the description in the previous question

Functional Groups With the CO Bond

A carbonyl group is composed of a carbon atom doublebonded to an oxygen atom. In this section, you will study the structures and properties of organic compounds that have the CO group. Aldehydes and Ketones Aldehydes and ketones both have the carbonyl functional g oup An aldehyde is an o ga c co pou d u c o a group. a de yde s a organic compound that has a double-bonded oxygen on the last carbon of a carbon chain. The functional group for an aldehyde is

 When the carbonyl group occurs within a hydrocarbon chain, the compound is a ketone. A ketone is an organic compound that has a double bonded oxygen on any double-bonded carbon within the carbon chain. The general formula for a ketone is RCOR2, where R and R2 are alkyl groups , y g p The functional group of a ketone is:

How to Name an Aldehyde

Step 1 Name the parent alkane. Always g give the carbon atom of the carbonyl y group the position number 1. Step 2 Replace the -e at the end of the e name of the parent alkane with -al. The carbonyl group is always given position y number 1. Therefore, you do not need to include a position number for it.

How to Name a Ketone

St 1 N Step Name th parent alkane. R the t lk Remember th t th b that the main chain must contain the CO group. Step 2 If there is one ketone group replace the -e at the group, end of the name of the parent alkane with -one. If there is more than one ketone group, keep the -e suffix and add a suffix such as -dione or -trione. dd ffi h di ti Step 3 For carbon chains that have more than four carbons, carbons a position number is needed for the carbonyl group. Number the carbon chain so that the carbonyl group has the lowest possible number

Practice

Carboxylic Acids
A carboxylic acid i an organic b li id is i compound with the following functional group:

This COOH group is called the carboxyl group. The general formula for a carboxylic acid is RCOOH.

How to Name a Carboxylic Acid

Step 1 Name the parent alkane. Step 2 Replace the -e at the end of the e name of the parent alkane with -oic acid. St 3 Th carbon atom of the carboxyl Step The b t f th b l group is always given position number 1. Name and number the branches that are attached to the compound.

HOMEWORKQUESTIONS2: HOMEWORK QUESTIONS 2: