1. Organic Chemistry
SCH4U- M. Kapica Spring 2017

2. Types of Carbon Primary (1◦) Carbon connected to one carbon atoms.
Secondary (2◦) Carbon connected to two carbon atoms.
Tertiary (3◦) Carbon connected to three carbon atoms.
How many primary, secondary, and tertiary carbons in the two different structures of C4H10 ?
Primary carbon = 3
Secondary carbon = 0
Tertiary carbon =1
Primary carbon = 2
Secondary carbon = 2
Tertiary carbon = 0

3. Isomerism
Constitutional Isomers (Structural Isomers) are different compounds of the same formula. There are two different structures for C4H 10 called isomers, because they contain different types of
carbon.
The different structures from the previous slide for the formula C4H10 is an example of Constitutional isomers.

4. Isomers – Example # 2 Pentane - C5H12
Draw all of the ways this compound could be structured. Then name the isomers!
(Hint – there are 3 isomers)

5. Isomers – Example # 2 (Solution)
Pentane - C5H12
Draw all of the ways this compound could be structured. Then name the isomers!
(Hint – there are 3 isomers)

6. Organic Compounds Organic compounds are molecular compounds of carbon.
Hydrocarbons are organic compounds that contain only carbon atoms and hydrogen atoms.
Ex. Butane (C4H10) or benzene (C6H6)

7. Why Study Organic Chemistry?
When you study organic chemistry you are studying the substances that make up your body and much of the world around you.
We can use the knowledge of organic compounds and synthesize them from inorganic compounds.

8. For example, the Perkin Reaction!

9. The Diels-Alder Reactions!
This is actually just steps out of a total of 23 steps  !

10. Classifying Hydrocarbons
We classify hydrocarbons based upon their covalent bonds between carbon atoms and functional groups.
Hydrocarbons
Aliphatics
Alkanes
Alkenes
Alkynes
Aromatics
Derivatives
ex. Alcohols, esters, amino acids

11. Alkanes
Simplest form of hydrocarbons that contain only single covalent bonds.
Said to be saturated hydrocarbons
The general formula for for all straight or branched chain alkanes is: CnH2n+2

12. Representing Organic Compounds
Model
Description
Empirical Formula
C5H12
Expanded Molecular Formula
CH3CH2(CH3)CH2CH3
Structural Formula
Condensed Structural Formula
Line Structural Formula

13. Naming Alkanes Use the IUPAC method Prefix + Root + Suffix
Based on number of carbon atoms
Use “-ane” as a suffix
Ex: methane ethane
Substituents are named with “yl” as a suffix Ex. Methyl ethyl
# C atoms
Root 1
Meth- 2
Eth- 3
Prop- 4
But- 5
Pent- 6
Hex- 7
Hept- 8
Oct- 9
Non- 10
Dec-
Substituents are side chains

14. Nomenclature of Alkanes
1. Find the longest continuous chain (parent chain or backbone). Determine the number of carbons in the parent hydrocarbon.
2. Identify any branches. Number the chain so that the substituent gets the lowest possible number.

15. Branched Chained Alkanes
Ex. What is the longest carbon chain in the following?

16. Branched Chained Alkanes
Ex. What is the longest carbon chain in the following?
 Pentane Chain  Hexane Chain

17. Number the substituents to yield the lowest possible number in the number of the compound.
(substituents are listed in alphabetical order)
4. Assign the lowest possible numbers to all of the substituents Name the substituents in alphabetical order. Lastly name the chain.

18. Rules for Naming Aliphatic Alkanes
We separate….
numbers from letters with a hyphen (-)
numbers from numbers by a comma (,)
When multiple branches of the same type are present:
Use the suffix di, tri, tetra etc. before the alkyl group
Ex.
a) 2,3-dimethylhexane
b) 2,3,3-trimethylpentane

19. 5. When both directions lead to the same lowest number for one of the substituents, the direction is chosen that gives the lowest possible number to one of the remaining substituents
6. If the same number is obtained in both directions, the first
group receives the lowest number

20. 7. In the case of two hydrocarbon chains with the same number of carbons, choose the one with the most substituents
8. Certain common nomenclatures are used in the IUPAC system You do not need to know these for this year.

21. Naming And Drawing Alkenes
Hydrocarbons that have at least one double bond between C atoms (C=C) in its chain.
These are unsaturated hydrocarbons since there is NOT the maximum possible number of H’s present.
General Formula  CnH2n
Use the same root with an – ene ending!

22. Naming Alkenes ( Same rules!)
Count the longest chain (that includes the double bond) and name it.
Use the suffix “ene”
Identify the position of the double bond (lowest number possible) and then branches.
If more than one double bond, number accordingly and use prefix ex. diene, for two double bonds
Note* The multiple bond takes priority of lowest number

23. Alkenes Example Draw the following: 8-methyl-3-nonene 1,4-octadiene
Name the following: a) b)

24. Other Examples of Alkenes
2-pentene
4-methylcyclohexene
2-ethyl-1-hexene
3-bromo-2-methyl-1-propene
5-ethyl-3-methyl-2-octene

25. Alkenes: Cis-Trans (Geometric) Isomers
Cis-Trans isomers occur when different groups of atoms are arranged around the C=C double bond.
Example:
2-butene
cis-2-butene
2 larger groups attached to same side
trans-2-butene
2 larger groups attached to opposite side

26. Naming and Drawing Alkynes
Hydrocarbons with at least one triple bond between C atoms (C C) in its chain.
Are unsaturated hydrocarbons
General Formula : CnH2n-2
Name following the same rules, however with an –yne ending. ( YAY!  )

27. Day 2 : Naming Hydrocarbons
Cyclic & Aromatic Hydrocarbons

28. Cyclic Hydrocarbons
Hydrocarbon ring structures are called cyclic hydrocarbons.
2 ends of a hydrocarbon chain react, thus we need to remove 2 H atoms from each end.
We follow the same naming conventions, however the prefix cyclo- is used in from of the root. Note, the root may be an alk-ane/ene/yne!
Ex. Steroids, cholesterol
steroid

29. Examples of Cyclic Hydrocarbons
Examples of cyclic alkanes.
Examples of cyclic alkenes
Note : Cyclic Alkynes are very rare. Usually they appear as intermediate in chemical reactions, due to high reactivity and low stability

30. Nomenclature of Cyclic Hydrocarbons
1. No number is needed for a single substituent on a ring. It is assumed that the substituent is on Carbon #1.
Note: The chain is actually pentane- and cyclobutane is the substituent.
2. Name the two substituents in alphabetical order

31. 3. If there are more than two substituents, the same rules apply
3. If there are more than two substituents, the same rules apply Number the carbons to give the lowest total number for substituent positions.

32. More Examples of Cycloalkanes

33. Naming Cycloalkenes
Double bond receives priority when numbering the carbons in the ring (just like with alkenes).
Branches get the lowest numbering sequence after the double bond.
“cyclo” + prefix + “ene”
List branches in alphabetical order, indicating the carbon number they are located on.

34. Examples of Cycloalkenes
cyclohexene
cyclopropene
CH2
CH3
CH2
CH3 1 4 2 3 3 2 1 4
3-ethylcyclobutene
3-ethyl-1,3-dimethylcyclobutene

35. Naming Aromatic Compounds
hydrocarbons containing one or more benzene rings ( C6H6) OR
all bonds are the same length
**we draw benzene like this**

36. NAMING AROMATIC COMPOUNDS
i. Benzene as a Substituent
if you have a really long carbon chain, it is easier to call the benzene ring a “phenyl” group
CH3
CH2 CH
eg)
4-phenylheptane
CH2 CH C ‗
CH3
3-methyl-5,5-diphenyloct-1-ene

37. ii. Benzene as a the Main Compound
if only one group is attached, give the alkyl name attached to “benzene”. No number is necessary.
eg)
CH3
methylbenzene

38. if there is more than one branch, number them so they get the lowest sequence and name them alphabetically.
CH3
CH2
eg)
1-ethyl-3-methylbenzene
CH3
CH2
1,3-dimethyl-5-propylbenzene

39. 1-ethyl-3-methylcyclohexane
CH3
C2H5
1-ethyl-3-methylcyclohexane

40. Properties of Alkanes non-polar and not-soluble in water.
Can be a solid, liquid or gas, depending on the number of carbon atoms
Relatively unreactive because the single bonds are very stable.
Uses: natural gas, BBQ’s, lighter fluid, gasoline. Also good for making plastics and lubricating substances.

41. Properties of Alkenes non-polar and not-soluble in water.
Lower boiling point than corresponding alkane because they have fewer electrons, which makes the London dispersion force of attraction weaker.
Eg. Ethane BP : *C Ethene BP : *C
More reactive than alkanes
Double bond has more electrons in the same area, resulting in greater repulsion and less bond stability.
Uses: plastics (PVC), steroids, welding torches

42. Properties of Alkynes Non-polar
Very Reactive ( more than alkanes and alkenes)
Triple bond has 6 electrons in the same area resulting in a high force of repulsion
Boiling points are higher than corresponding alkanes and alkenes, because of their linear structure and the nature of the triple bond.

43. Properties of Aromatics
Non-polar
The benzene ring structure is very stable.
Aromatics are characterized by strong aromas.
Uses : ASA, amphetamines, adrenaline, benzocaine(anesthetic), moth balls, TNT, wintergreen, menthol, vanilla, cinnamon , SPF in sunscreen

44. Day 3: Naming Organic Compounds
Alcohols
Alkyl Halides
Carboxylic Acids
Aldehydes
Ketones

45. Naming Alcohols Functional group: -OH, hydroxyl group
Naming: Replace the “e” ending of the parent alkane chain with “ol”.
CH3OH methanol
CH3CH2OH ethanol
CH3CH2CH2OH 1-propanol
NOTE: the position of the OH group is indicated for different structural isomers.
Polyalcohols contain more than one hydroxyl group: the suffixes -diol and -triol are added (example: 1,2-ethanediol)

46. Properties of Alcohols
-OH group is quite polar and capable of forming hydrogen bonds with water.
Therefore, low molecular mass alcohols (4 or less C’s) are quite soluble in water, but alcohols with 5 or more C’s are usually not very soluble in water because of the long, non-polar hydrocarbon chain.
Have boiling points much higher than corresponding aliphatics, due to hydrogen bonds
Due to the non-polar hydrocarbon chains, long chain alcohols are soluble in non-polar solvents.
eg) methane (CH4) BP = *C
methanol (CH3OH) BP = 65*C

47. Types of alcohols: Primary, Secondary and Tertiary
primary alcohol: the –OH group is bonded to a carbon that is bonded to one other carbon atom
secondary alcohol: the –OH group is bonded to a carbon that is bonded to two other carbon atoms
tertiary alcohol:the –OH group is bonded to a carbon that is bonded to three other carbon atoms

48. Examples of Alcohols H OH C H OH C CH3 butan-2-ol Or 2-butanol
3-methylbutan-2-ol
3-methyl-2-butanol

49. an unusual case: H OH C CH3 OH 2-methylbutane-2,3-diol
2-methyl-2,3-butandiol
an unusual case: OH
phenol

50. Organic Halides (R-X)
Alkane in which one or more hydrogen atoms have been replaced with halogen atoms, F, Cl, Br, or I.
Examples:
chloroalkanes; CH3Cl, CH2Cl2, CHCl3, CCl4
chlorofluorocarbons (CFCs)
Naming: Halides substituents are named as all other substituent types. F - fluoro Cl - chloro Br - bromo I iodo
1,1,2-trichloroethene

51. CFC’s Group of compounds known as chlorofluorocarbons
Widely used as refrigerating agents.
Main source of ozone depletion
Very stable
Insoluble in water (rain)
As a result – can travel from the lower atmosphere up until they reach the ozone layer
Unreactive at Earth’s surface but if they get into the stratosphere they can be broken down by high energy UV radiation which leads to release of highly reactive chlorine

52. Properties of organic halides
C-X bond is more polar than a C-H bond
Higher solubility in a polar solvent

53. Carboxylic acids, R-COOH
Functional group: the carboxyl group
(-COOH)
Organic acid
Weak acids found in citrus fruit, crab apples, etc.
Most common: vinegar

54. Naming Carboxylic Acids
Step 1: Name the parent alkane
Step 2: Replace the “e” of parent alkane with “oic acid”.
Step 3: The carbon atom of the carboxyl group is always given position number 1. Then, name and number the branches that are attached to the compound.

55. eg) OH ║ O C H
methanoic acid OH ║ O C H
ethanoic acid

56. OH ║ O C
benzoic acid O H H H ║ I C C C C OH H H H
4-iodobutanoic acid

57. Properties of Carboxylic Acids
Polar compounds
due to presence of the polar –OH and C=O bonds
Hydrogen bonding between carboxylic acid molecules and water molecules
First four simple carboxylic acid are miscible with water. Solubility then decreases as the number of carbon atoms increases.
Melting and boiling points of carboxylic acids are very high
Because of the strong hydrogen bonds between molecules

58. Comparison of melting and boiling point of carboxylic acid with other organic compounds

59. Explaining Acidic Properties of Carboxylic Acids
–OH group in carboxylic acid does not behave like the basic hydroxyde ion, OH-
Oxygen has a high electronegativity and there are 2 oxygen atoms present to help carry the extra negative charge that is caused when a positive hydrogen atom dissociates.

60. ALDEHYDES AND KETONES
“carbonyl” functional group:
Aldehydes Ketones

61. Aldehydes, IUPAC nomenclature
Parent chain = longest continuous carbon chain containing the carbonyl group; alkane, drop –e, add –al.
(note: no locant, -CH=O is carbon #1.)
CH3
CH3CH2CH2CH=O CH3CHCH=O
butanal methylpropanal
H2C=O CH3CH=O
methanal ethanal

62. Ketones: IUPAC nomenclature:
Parent = longest continuous carbon chain containing the carbonyl group. Alkane, drop –e, add –one. Prefix a locant for the position of the carbonyl using the principle of lower number.

63. Aldehyde vs Ketone

64. Aldehydes and ketones in the chemistry of carbohydrates
Carbohydrate literally means a "hydrate" of carbon,
compounds with the empirical formula CH2O.
Glucose and fructose are carbohydrates with the formula C6H12O6.

71. Day 4: Naming Organic Compounds
Esters
Ethers
Amines
Amides`

72. Esters, R-COO-R’ Functional group: alkylated carboxyl group, -COOR’
Low molar mass esters have very pleasant fragrances
Used in perfumes, soaps, cosmetics, etc.
Made from the reaction of alcohols and carboxylic acids

73. Naming Esters
Step 1: Identify the main part of the ester, which contains the C=O group. This part comes from the parent acid. Begin by naming the parent acid.
Step 2: Replace the –oic acid ending of the name of parent acid with “oate”
Step 3: The second part of an ester is the alkyl group that is attached to the oxygen atom. It came from the alcohol. Name this as you would name any other alkyl group.
Step 4: Put the two names together. Note that esters are named as two words.

75. Examples:
octyl ethanoate
(oranges)
pentyl butanoate
(apricots)

76. Examples of Esters: e.g. dietary fats are triglycerides (esters) O =
Glycerol =
RCO-CH2 = O
CH3(CH2)16C HO
CH2 OH O =
RCO-CH = O
CH3(CH2)16C HO OH CH O =
RCO-CH2 = O
CH3(CH2)16C HO OH
CH2
Fatty acids

77. Properties of Esters Polar molecules
No hydrogen bonding with other molecules due to absence of –OH group
Slightly soluble in water (chains of three or four carbons) due to polarity
Low boiling points due to absence of hydrogen bonds (volatile liquids at room temperature)

78. O ║ C H
ethyl butanoate O ║ C H
CH3
propyl propanoate

79. O ║ C H
CH3
ethyl 2-methylbutanoate

80. Ethers
William Thomas Green Morton was an American dentist who first publicly demonstrated the use of inhaled ether as a surgical anaesthetic in 1846.

81. Ethers Functional group: R-O-R’ (alkoxy group)
Absence of the -OH groups, makes hydrogen bonding impossible.
Slightly polar due to polar C-O bond and V-shaped of the C-O-C bond.
Unreactive
Able to mix with polar and non-polar solvents

82. Naming ethers
Add “oxy” to the prefix of the SMALLER hydrocarbon group and join it to the alkane name of the larger hydrocarbon group.
As molar mass of alcohols or ethers increase, BP increase. Alcohols and ethers are structural isomers.

83. Ethers with Substituents

84. Just for fun…
Another way to name ethers is by placing the prefixes for the two alkyl groups in front of the word “ether”
Example:
CH3-O-CH2CH3
CH3CH2-O-CH2CH2CH2CH3
methyl ethyl ether
ethyl butyl ether

85. Organic Chemistry
Amines and Amides

86. Bonding characteristics of nitrogen atoms in organic compounds
We saw already that carbon atoms (Group 4A) form four bonds to other atoms in organic compounds.
And oxygen atoms (Group 6A) form two bonds.
Nitrogen atoms (Group 5A) require three bonds to give them octets. Normally, nitrogen atoms are involved in three covalent bonds to other atoms.

87. Structure and classification of amines
Amines are organic derivatives of ammonia (NH3), in which one or more alkyl, cycloalkyl, or aromatic groups replace hydrogen and bond to the nitrogen atom.

88. Amines; -NH2, -NHR, or -NR2
Classified as primary, secondary or tertiary depending on how many alkyl groups are attached to the nitrogen atom.
Primary amine has one alkyl group and two hydrogen atoms attached to the nitrogen.
Secondary amine has two alkyl groups and one hydrogen atom attached to the nitrogen.
Tertiary amine has three alkyl groups attached to the nitrogen atom.

89. Classification of Amines

90. Naming Amines
Identify the largest hydrocarbon chain attached to the nitrogen atom as the parent alkane.
Replace the –e with a new ending – amine. Include a position number. C-1 is located nearest to the nitrogen. N is not always attached to carbon 1.
Name the other alkyl group(s) attached to the nitrogen atom. Instead of position numbers, use the letter N- to locate the groups. If two identical alkyl groups are attached to the nitrogen atom, use N,N- .

91. Structure and classification of amines
Some examples. First, 1o amines
4-C chain (“butane”; - “e” + “amine”)
# to indicate placement of NH2 group

92. Structure and classification of amines
For di- and trisubstituted amines, the non-parent chains are indicated as N-bonded:

93. Structure and classification of amines
For diamines, the molecule is named as an “alkane-diamine” with NH2 groups numbered.
And for cases where NH2-substituted alcohols or other compound cases are involved, the NH2-group is called an “amino” substituent.

94. Structure and classification of amines
In cases where substituted parent chains are encountered, the substituents are named at the beginning of the compound’s name:
Parent chain: pentane
Amino-position: C-2 of parent chain
CH3- substituents on parent chain (C-4) and N

95. Draw each of the following
A) 2-pentanamine
B) cyclohexanamine
C) N-methyl-1-butanamine
D) N,N-diethyl-3-heptanamine

96. Properties of Amines
C-N and N-H bonds are polar, therefore amines are usually polar.
Presence of one or more N-H bonds allows for H-bonding.
Amines are found widely in nature. They are also often toxic, and are commonly found in plants with medicinal properties
Amines with low molar masses have distinctive fish odours.
For example, cadavarine- contributes to the odour of DECAYING FLESH!

97. Physical properties of amines
Amines tend to be gases for low molecular weight cases (e.g. up to (CH3)3N, trimethylamine) and many heavier ones are liquids at room temperature.
One very noticeable thing about amines is that they tend to exhibit strong odors. For example, some have a “fishy” smell

98. Physical properties of amines
Amine boiling points are intermediate of those for alcohols and alkanes of similar molar mass.
Because of the presence of N-H bond(s) in primary and secondary amines, hydrogen-bonding is sometimes possible; however, because N is not as electronegative as O, the N-H bond is not as polar as an O-H bond (weaker H-bonding).

99. Examples of Amines
Adrenaline: hormone produced by human body under stress
Also responsible for odours of decay and decomposition
Weak bases (like ammonia, they can accept a proton)
Explains why vinegar and lemon juice (acids) can neutralize the fishy smell of seafood (caused by basic amines)
Epinephrine is a "fight or flight" hormone, and plays a central role in the short-term stress reaction. It is released from the adrenal glands when danger threatens or in an emergency, hence an Adrenaline rush. Such triggers may be threatening, exciting, or environmental stressor conditions such as high noise levels, or bright light and high ambient temperature
When in the bloodstream, it rapidly prepares the body for action in emergency situations. The hormone boosts the supply of oxygen and glucose to the brain and muscles, while suppressing other non-emergency bodily processes (digestion in particular).
It increases heart rate and stroke volume, dilates the pupils, and constricts arterioles in the skin and gastrointestinal tract while dilating arterioles in skeletal muscles. It elevates the blood sugar level by increasing catabolism of glycogen to glucose in the liver, and at the same time
It increases heart rate and stroke volume, dilates the pupils, and constricts arterioles in the skin and gastrointestinal tract while dilating arterioles in skeletal muscles. It elevates the blood sugar level by increasing catabolism of glycogen to glucose in the liver, and at the same time When in the bloodstream, it rapidly prepares the body for action in emergency situations. The hormone boosts the supply of oxygen and glucose to the brain and muscles, while suppressing other non-emergency bodily processes (digestion in particular).

100. Amides; R-CO-NR2 (R = H or alkyl groups)
combination of a carboxylic acid and an amine

101. Structure and classification of amides
Amides possess a functional group that consists of a C=O (carbonyl) directly bound to a nitrogen:
The amide functional group involves a nitrogen atom (and lone pair), but unlike an amine, the nitrogen center is not basic, due to the electron-withdrawing effect of the C=O group.

102. Classifying Amides

103. Structure and classification of amides
In terms of their structure, amines may be aromatic (benzene substituents); for example, benzamide:
They may also be cyclic, or even involve multiple amide groups in a single ring:
A d-lactam

104. Nomenclature of amides
IUPAC system for naming amides:
Like esters, amides are made using carboxylic acids. The portion that comes from the carboxylic acid is named as a carboxylic acid first, before dropping the “-oic acid” from the name and adding “-amide”
Substituents attached to the nitrogen are prefixed with “N-” to indicate their position; other substituents on the parent chain are named as part of the parent chain (unlike for amines).

105. Nomenclature of amides
Some examples:
For aromatic cases:

106. Selected amides and their uses
Urea is one of the simplest amides, formed by reaction between CO2 and ammonia in a series of metabolic reactions.
Acetominophen is an aromatic amide
Barbiturates derive from barbituric acid (sedatives/tranquilizers) are cyclic amides, made from urea and malonic acid:

107. Examples

108. Physical properties of amides
Amides do not have a basic non-bonding pair of electrons, like amines (as mentioned)
The simplest amides (methanamide, N-methyl, and N,N-dimethyl derivatives) are liquids at room temperature, and all unbranched amides having 2 or more carbons on their C-chain side are solids.
The secondary and teritary amides have lower melting points, with tertiary amides having lower melting points than secondary amides (less opportunity for H-bonding).

109. Physical properties of amides
4 locations on a primary amide group
that may participate in intermolecular
H-bonding

110. Examples of Amides
Acetaminophen (an amide) is a main component of many painkillers.
Urea is another example of an amide. It was the first organic compound to be synthesized in a laboratory.
A component of fertilizer and animal feed, providing a relatively cheap source of nitrogen to promote growth
A raw material for the manufacture of plastics, to be specific, urea-formaldehyde resin
A raw material for the manufacture of various glues (urea-formaldehyde or urea-melamine-formaldehyde); the latter is waterproof and is used for marine plywood
An alternative to rock salt in the de-icing of roadways and runways; it does not promote metal corrosion to the extent that salt does
An additive ingredient in cigarettes, designed to enhance flavour
A browning agent in factory-produced pretzels

111. Examples of Amides
A component of fertilizer and animal feed, providing a relatively cheap source of nitrogen to promote growth
An alternative to rock salt in the de-icing of roadways and runways; it does not promote metal corrosion to the extent that salt does

112. Examples of Amides
A raw material for the manufacture of plastics, to be specific, urea-formaldehyde resin
A raw material for the manufacture of various glues (urea-formaldehyde or urea-melamine-formaldehyde); the latter is waterproof and is used for marine plywood

113. Examples of Amides
An additive ingredient in cigarettes, designed to enhance flavour
A browning agent in factory-produced pretzels

114. Organic Chemistry Part 2 :
Organic Reactions

115. Organic Chemistry Reactions
Addition
Elimination
Substitution

116. ***Two compounds usually react to form One major product
Addition Reactions
Reactions in which atoms are added to a carbon-carbon double or triple bonds. Common atoms that can be added to an alkene or alkyne:
H and H (From H2(g))
H and OH (From H2O)
H and X (From Acid Halides , H-X , where X= Cl,Br,I, F)
X and X from (From Diatomic Halides X2) where X= Cl, Br, I
***Two compounds usually react to form One major product

117. Example 1 : Addition of H2 (g)
2-butene butane
Addition of H2 takes place in the presence of Pt or Pd catalysts

118. Example 2: Addition of Diatomic Halide

119. Example 2: Addition of Diatomic Halide+ +

120. Example 2 : Excess Diatomic Halide

121. Markovnikov’s Rule: R-X & H2O
“the rich get richer”
The carbon atoms with the largest number of hydrogen's bonded to it – gets the hydrogen.
Major Product

122. Example 3: Acid Halide Addition

123. Example 3: Alkyl Halide Addition
50% 2-bromo pentane
50% 3-bromo pentane

124. Example 4: Addition of Water

125. Elimination Reactions
Reactions in which atoms are removed from an organic molecule to form a double bond (reverse of addition reaction). One reactant breaks into two products.
Alcohols  Alkene (in presence of heat and strong acid)
Alykl Halides Alkenes (Heat and Strong Base_
*** One reactant usually breaks to give two products

126. Example: Alcohols  Alkenes

127. Elimination Reaction: Alkyl Halides
Undergo elimination to produce alkenes in the presence of heat and strong bases.
Bromoethane ethene hydrobromic acid

128. Example: Asymetric molecules
Elimination reaction of 2-Bromobutane: Hydrogen can be removed from either C-1 or C-2
“ The hydrogen that is most likely to be removed is from the carbon atom with the most carbon-carbon bonds”

129. Substitution Reactions
Reaction in which a hydrogen atom or functional group is replaced by a different atom or functional group- often halogens.
Look for: two compounds react to form two different compounds
Carbon atoms are bonded to the same number of atoms in the product on reactant

130. Substitution: Alcohols
When an alcohol reacts with an acid that contains a halogen (eg. HCl or HBr), the halogen atom is substituted for the hydroxyl (-OH) group of the alcohol.

131. Substitution: Haloalkanes
A haloalkane can undergo a substitution reaction with a hydroxide ion to produce an alcohol.

132. Substitution: Alkanes
Alkanes are relatively unreactive. Therefore, considerable amounts of energy for example, from the presence of UV light can, chlorinate or brominate a substance.

133. Substitution: Aromatics
Most aromatics are fairly stable. They will undergo substitution reactions with chlorine or bromine, but only in the presence of a catalyst.