unit 3: hydrocarbon derivatives name: · naming alcohols 1. indicate location of -oh group (number...
TRANSCRIPT
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Chemistry 2202 Unit 3: Hydrocarbon Derivatives Name: _________________
Hydrocarbon Derivatives
- organic compounds containing C, H, and at least 1 other atom
- one of the H atoms is replaced by another atom to form a derivative
- includes alcohols, ethers, aldehydes, ketones, carboxylic (organic) acids, alkyl
(organic) halides, esters, amines, amides
- each hydrocarbon derivative has an alkyl stem and a functional group
Alkyl Stem - the continuous chain of C atoms on which a functional
group is attached to make it a HC derivative
Functional Group - an identifiable arrangement of atoms that gives a
compound certain chemical properties
Organic Compounds
Hydrocarbon Derivatives Pure Hydrocarbons
Alkyl Halides Aldehydes
Ketones Alcohols
Ethers Organic Acids
Esters Amines
Amides
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Alkyl Halides - a.k.a. halocarbons and organic halides
- Basic Formula R-X R - represents the parent HC chain
X - represents functional group
- Functional group - halogen atom such as F, Cl, Br, I
Properties
- few of these compounds found in nature
- mostly synthetic
- toxic, carcinogenic, flammable
- widely used as both anesthetics and insecticides
- involved in substitution reactions
Examples
- Chloroethane - (C2H5Cl) or (CH3CH2Cl) - local anesthetic - rapid cooling
of the skin deadens the nerve endings reducing pain
transmission to the brain.
- CFCs - chlorofluorocarbons
- used as refrigerant (freon)
- destroy ozone layer
- DDT - dichlorodiphenyltrichloroethane
- insecticide used between 1950s and 1970s (non-
biodegradable)
- leads to bioamplification in organisms
- PCB’s - polychlorinated biphenyls
- used as insulating fluid in electrical transformers and capacitors
- breaks down very slowly
- severe health effects
- strictly regulated in Canada (western world)
Naming Alkyl Halides
1. Indicate position of halogen atom on the longest continuous HC chain with the
halogen (number chain to give the atom lowest #).
2. Identify the halogen but change ending -ine to -o.
e.g. fluorine –> fluoro
If more than one halogen, use di, tri, tetra.
e.g. fluorine –> difluoro
3. Complete the name by naming C chain with appropriate prefix.
a. (Ex: 3 Carbons - propane)
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Examples
Ex 1:
Name: 2,3,4-tribromo-3-ethyl hexane
Ex 2:
Name: 2,3-dibromo-2-methyl butane
Ex 3:
Name: 1,4-difluoro cyclohexane
Ex 4:
Name: 1,3-dibromo-4-methyl cyclohexane
Ex : 5
Name: 2,3,4-trichloro-2-bromo-3-
ethylpentane
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Alcohols
Formula: R-OH where R - represents HC parent chain
OH - represents hydroxyl functional group
- OH not the same as hydroxide ion (OH-)
- based on ‘alkane’ parent chain
Properties
- liquids at room T
- flammable
- boil at higher T b/c of H-bonds
- polar (-OH) and non-polar (HC) ends
- short chains soluble in water
Examples
Methanol - CH3OH
- “wood alcohol” historically made by heating wood shavings in the
absence of air
- used as a fuel in some race cars
- toxic to humans if inhaled or drank
- drink 10 mL - blindness
-drink 30 mL - death
Ethanol - C2H5OH
- “grain alcohol” historically made by fermentation, where yeast cells
break down sugar to form ethanol
- solvent in drugs, food preparation, varnishes, perfume, flavouring
- intoxicating substance in “alcohol”
- depressant drug, liver damage, behaviour changes
- laboratory ethanol must be “denatured” (ex: methanol added)
Ethylene glycol
- C2H4(OH)2
- rubbing alcohol
- antifreeze -> -17.4oC
- add water -> -36oC
- kidney failure if ingested
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Naming Alcohols
1. Indicate location of -OH group (number HC chain to get lowest possible #).
2. Finish name as if naming an alkane, but change ending ‘e’ to ‘ol’.
e.g. 2 C chain - ethane -> ethanol
3 C chain with OH on C#2 = 2-propanol
Ex 1
Name: Methanol
Ex 2
Name: Ethanol
Ex 3
Name: 2-Propanol (rubbing alcohol)
Ex 4
Name: Propanol (wax solvent / paint
laquer)
Ex 5
Name: 2-methyl-2-butanol
OH
Ex 6
Name: 3-methyl-1-butanol
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Alcohol Type
Depending on the position of the hydroxyl (OH) group, the alcohol can be either
primary, secondary or tertiary in type.
Primary Alcohol - the hydroxyl group is bonded to a carbon atom
that is bonded to only one other carbon atom.
Secondary Alcohol - the hydroxyl group is bonded to a carbon atom
that is bonded to two other carbon atoms.
Tertiary Alcohol - the hydroxyl group is bonded to a carbon atom
that is bonded to three other carbon atoms.
As well, depending on the number of hydroxyl groups contained within alcohol molecules,
the following prefixes are required.
One -OH’s ol
Two -OH’s diol
Three -OH’s triol
Four -OH’s tetrol
Examples
Formula # hydroxyl groups (other) Alcohol Name
OHOH
two hydroxyl groups
2 carbon HC chain 1,2 - ethandiol
OH
OHOH
three hydroxyl groups
4 carbon HC chain 2,2,3 - butantriol
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Examples
Formula # hydroxyl groups (other) Alcohol Name
OH
ethanol
OH
one hydroxyl group
3 carbon HC chain 2 - propanol
OH
OH
1,2 - propandiol
OHOH
two hydroxyl groups
3 carbon HC chain 2,2 - propandiol
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OH
one hydroxyl group
one methyl group
3 carbon HC chain
2 - methyl -1- propanol
or
2 - methyl propanol
OH
2 - butanol
OH
OH
OH
2,3,4 - pentantriol
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Chemistry 2202
Alcohols
Questions: Complete the following chart. Name: ____________________
Formula # hydroxyl groups
# C in HC chain
Alcohol Name
2-methyl-2-propanol
1 hydroxyl group on C 1
4 C chain
2,2-dimethyl-1-butanol
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2-butanol
Methyl on C 3
Hydroxyl on C 2
1-ethanol
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Ethers
- two CH groups that are joined by an oxygen atom.
- basic formula: R-O-R
where R - represents the parent carbon chain
O - represents the functional group
Properties
- highly flammable
- soluble in water
- liquids at room T
Examples
- Diethyl ether (C4H10O)(CH3 CH2 O CH2 CH3)
- used as an anesthetic for more than 100 years (until 1950s)
- flammable and causes nausea
Other Examples
Ether Common Use
C2H4O fungicide
C7H8O Perfume
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C8H8O vanilla flavouring agent
C14H12O3 sunscreen ingredient
C15H20O3 sex pheromone in American cockroaches
C21H30O2 THC
C50H70O14 marine neurotoxin secreted by dinoflagellates; “red tides”
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Naming Ethers
1. Name each C-H chain using the longest alkyl (CH) group as the parent chain.
If 2 chains same - add prefix “di.”
If 2 chains different - list in alphabetical order as one word.
2. Add the word ‘ether’ to end.
Examples
O CH3CH
3
dimethyl ether
O
ethylpropyl ether
O
ethylmethyl ether
O
diethyl ether
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dipropyl ether
O
dipentyl ether
O
methylpropyl ether
ethylpropyl ether
O
butylethyl ether
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Chemistry 2202
Worksheet 1: Alkyl Halides, Alcohols and Ethers
Name:____________________
Instructions: Complete the following chart.
Structural Diagram Compound Type Compound Name
1
2,2-dimethyl-4-propyl-
3-heptanol
2
2,2-dibromopropane
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3
2-methyl-1-butanol
4
OH
OH
5
3-chloro-2,4-
difluorooctane
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6
O
7
dimethylether
8
OH
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9
butylpentylether
10
Cl F
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Amines
- an organic compound formed from the decomposition of amino acids by bacteria.
- compounds smell like rotting fish, and other peculiar generally disagreeable odours
-also cadaverine, or rotting flesh(NH2(CH2)5 NH2)
-derivatives of ammonia NH3
-found commonly in nature
- basic formula is R-NH2 where R represents parent carbon chain
NH2 represents functional group
Properties
-usually polar molecules
-miscible in water
-solubility decreases with length of parent chain
Naming Amines
1. Count the number of carbon atoms in the chain & use appropriate prefix.
2. Name as an amine by dropping ‘e’ and adding ‘amine’ to the name.
Examples
NH2
methanamine
NH2
ethanamine
NH2
hexanamine
NH2
propanamine
NH2
butanamine
NH2
nonanamine
NH2
heptanamine
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Amide
-these compounds can be found in protein molecules
-are the peptide bonds that join amino acids to each other
-basic formula R = O where R represents the parent chain
O and NH2 represent the functional group
NH2 (carbon atom double bonded to an O atom & single bonded to an N group)
Properties
-usually polar molecules
-polar end is soluble in water
-solubility of molecule decreases with increasing length of parent chain
Examples
-Acetaminophen - pain killer
-Urea - first organic compound produced synthetically
- found naturally in mammal urine
Naming Amides
1. Count the number of carbon atoms in the parent chain and use appropriate prefix.
2. Name as an amine by dropping ‘e’ and adding ‘amide’ to the name.
Examples
ethanamide
methanamide
butanamide
hexanamide
nonanamide
octanamide
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Chemistry 2202
Worksheet 2: Amines and Amides Name:____________________
Instructions: Complete the following chart.
Structural Diagram:
Name: 2-hexanamine
Structural Diagram:
Formula: CH3 (CH2)4CO(NH2)
Name:
Structural Diagram:
Name: 4-nonanamine
Structural Diagram:
CH3CH2CH(NH2)CH3
Name:
Structural Diagram:
Name: methanamide
Structural Diagram:
Name: cyclopentamine
Structural Diagram:
Name: hexanamide
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Aldehydes
- an organic compound with a double bonded oxygen atom on the end carbon of a
carbon stem
- the functional group is the oxygen atom (carbonyl group)
- the basic formula is:
R = O where R represents the parent chain
O represents the functional group
Examples
Methanal (CH2O)
- common name “formaldehyde”
- historically used to preserve biology specimens
-currently used to preserve bodies
- causes cancer and mutations in animals
- methanol becomes methanal in body
Ethanal (C2H4O)
- ethanol becomes ethanal in the body
- “hangover” - headaches, vertigo, gastric upset
Naming Aldehydes
1. Identify longest C chain and use prefix.
e.g. 1 C - meth
2. Replace ending -e with -al.
e.g. methane –> methanal
Examples
O
ethanal
O
hexanal
O
3-methylbutanal
O
CH2
methanal
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Ketones - an organic compound with a double bonded oxygen atom on any carbon within the
parent carbon chain.
- functional group is oxygen atom within the molecule
- the basic formula is
R - C - R where R represents the parent chains
O represents the functional group
O
Examples
- Propanone (CH3COCH3)
- common name “acetone”
- solvent in nail polish remover, varnish, plastic cement
Naming Ketones:
1. Identify longest C chain and name with prefix
e.g. 3 C - prop
2. Indicate the position of the carbonyl group
3. Replace ending -e with -one.
e.g. 2 - propanone
Examples
O
propanone
O
2 - butanone
O
3 - hexanone
O
4 - heptanone
O
4 - octanone
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Chemistry 2202
Worksheet 3: Aldehydes and Ketones Name:____________________
Instructions: Complete the following chart.
Structural Diagram Compound Type Compound Name
1
heptanal
2 O
3
3-methylpentanal
4
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5
2,2-dimethyl-4-octanone
6 O
7 4,4-diethylhexanal
8
O
9
3-ethyl-2-pentanone
10
O
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Carboxylic Acids
(a.k.a. Organic Acids)
- an organic compound with a double bonded oxygen atom and a hydroxyl (OH) group
at the end of a parent carbon chain. -
- functional group -COOH
- basic formula
where R represents the parent chain
COOH represents the functional group (aka carboxyl group)
Properties
- polar, H-bonds, acidic
- sour, tangy taste
- strong odours
- found in citrus fruit, crabapples, rhubarb
Examples
- Methanoic Acid (HCOOH)
- common name “formic acid”
- irritant in bee/insect stings
- used to remove hair from animal hides
- Ethanoic Acid (CH3COOH)
- common name “acetic acid”
- produced when wine turns sour
- pungent odour in vinegar
- Butanoic Acid (CH3CH2CH2COOH)
- rancid butter, dirty feet smell
- police dogs follow carboxylic acid in sweaty feet
- Octanoic Acid
- common name “stearic acid”
- extracted from beef fat
- used to make cheap wax candles
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Naming Organic Acids
1. Name the C chain with prefix.
e.g. 3 C - prop
2. Change -e to -oic acid.
e.g. propane - propanoic acid
Examples O
OH
propanoic acid
O
OH
butanoic acid
O
OH
pentanoic acid
O
OH
octanoic acid
O
OH
methanoic acid
O
OH
heptanoic acid
O
OH
hexanoic acid
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Esters - an organic compound with a double bonded oxygen atom and a single bonded oxygen
atom in the middle of a parent carbon chain.
- formed by reacting an carboxylic acid with an alcohol
- the basic formula is
R – C - O - R where R - C = O represents acid side
O - R represents alcohol side
O
Properties
- many esters have pleasant aromas and flavours
- found naturally in fruits and flowers
- used in foods, cosmetics, perfumes, synthetic fibers, and solvents
Examples
Chemical Formula Compound Name Use
C5H10O2 methyl butyrate apple aroma
C5H10O2 n-propyl acetate pear aroma
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C6H8O6 methyl salicylate wintergreen
C7H12O2 ethyl propionate rum aroma
C7H14O2 isoamyl acetate banana,
C9H8O4 ethyl acetate fingernail polish remover
C10H12O2 ethyl phenylacetate honey aroma
C10H20O2 octyl acetate orange aroma
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Naming Esters
- We separately name the acid (=O) side and the alcohol side (-O with H dropped from
OH to allowing bond with carbon from acid side)
1. Name C chain from alcohol (side with C-O) like a branch
e.g. 3 C –> propyl
2. Name C chain from acid (side with C=O), but change ending -e to -oate
e.g. 2 C –> ethane –> ethanoate
3. Combine both parts
propyl ethanoate
Examples
O
O
propyl propanoate
O
O
propyl ethanoate
O
O
methyl butanoate
O
O
methyl octanoate
O
O
ethyl ethanoate
O
O
propyl methanoate
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Chemistry 2202
Worksheet 4: Carboxylic (Organic) Acids and Esters
Name:____________________
Instructions: Complete the following chart.
Structural Diagram Compound Type Compound Name
1
butanoic acid
2
O
OH
3
2,4-dimethylheptanoic acid
4 O
OH
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5 butylpentanoate
6 O
O
7
propyl methanoate
8 O
O
9
benzoic acid
10 O
O
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Chemistry 2202
Worksheet 5: Amines, Amides, Aldehydes, Ketones, Organic Acids and Esters
Name:________________________
Instructions: Name each structure below, then identify the type of hydrocarbon derivative that it is.
1
NH2
Type: __________________________
Name: __________________________
2
O
Type: __________________________
Name: __________________________
3
O
O
Type: __________________________
Name: __________________________
4
O
OH
Type: __________________________
Name: __________________________
5
O
Type: __________________________
Name: __________________________
6
NH2
O
Type: __________________________
Name: __________________________
7
OH
O
Type: __________________________
Name: __________________________
8
O
Type: __________________________
Name: __________________________
9
NH2
Type: __________________________
Name: __________________________
10
O
O
Type: __________________________
Name: __________________________
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Chemistry 2202
Worksheet 6: Hydrocarbon Derivatives Review Name:____________________
1. Complete the following chart by writing the name of the compound.
1
OH
Name:___________________________
2 O
O
Name:___________________________
3
O
OH
Name:___________________________
4
O
Name:___________________________
5 O
Name:___________________________
6 Cl
Br
Name:___________________________
7 NH2
O Name:___________________________
8
NH2 Name:___________________________
9
OH
Name:___________________________
10 Cl
Br
F
Name:___________________________
11
O
Name:___________________________
12 OH
OHOH Name:___________________________
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2. Complete the following chart by drawing the structural formula of the compound.
1
1-propanol
2
methyl propyl ether
3
3-decanone
4
1,2-difluoropropane
5
propyl methanoate
6
2-pentanol
7
ethanal
8
propanoic acid
9
2-bromopropane
10
2-pentanol
11
butanal
12
2-methylpentanoic acid
13
dimethyl ether
14
methyl ethanoate
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Polymerization
Polymerization
- The process of joining monomers to form polymers.
- Monomers - small carbon based molecules that combine like links in a chain that
can be joined to form polymers
- Polymers - literally means many parts
- macromolecules
- can be composed of thousands of monomers
- can be composed of multiple types of monomers
-found in oils, tars, resins, rubber, plastics, etc.
-Two main methods:
1. Addition Polymerization
2. Condensation Polymerization
1. Addition Polymerization -Occurs when unsaturated monomers join together to form polymers
-The double or triple bond of the unsaturated compound is broken and the
individual molecules join together.
General Equation
Monomer + Monomer + H2 ----> Polymer
Example 1: Polymerization of ethene to produce polyethylene
Example 2: Polymerization of ethene and propene
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2. Condensation Polymerization
-Occurs when two different types of monomers join together to form
polymers.
-monomers contain a hydroxyl functional group.
-Water is condensed as a product out of the reaction.
-Monomers bond at site where atom is removed.
General Equation
Organic Acid + Alcohol ----> Polymer +Water
Example:
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Natural Polymers
-Carbohydrates
-sugars; used for energy
-photosynthesis
6CO2 + 6H2O —> C6H12O6 + O2 glucose
Glucose - main type of sugar produced during photosynthesis
- stored in animals as glycogen
- stored in plants as cellulose and starch
- polymers of glucose are called polysaccharides
-Cellular respiration - reverse polymerization
-Proteins
-composed of amino acids
-polymers used for cell and muscle structure
-examples include hormones, enzymes, muscles, hair, ligaments, antibodies,
etc.
- vital for the normal functioning of the body
-used to transport nutrients throughout the body
-used to help the body fight diseases, etc.
-Lipids
-composed primarily of long chain saturated fatty acids
-major building blocks of cell membranes in animal(human) bodies
-used to regulate our metabolism
-used by the body to store energy
Synthetic Polymers
- often referred to as plastics
- most, however can be categorized into three main categories
1. thermoplastics - generally elastic and flexible
- turns to liquid when heated
- freezes to a glassy state
2. thermosets - materials that irreversibly cure
- curing process transforms polymer
- examples include vulcanized rubber, epoxy
3. elastomers - polymers with high elasticity properties
- material has ‘memory return’ capability
- examples include natural rubber
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Chemistry 2202
Unit 3: Hydrocarbon Derivative Reactions Name:_________________
Recall: Pure Hydrocarbon Reaction Types
1. Cracking
2. Reforming
3. Addition
4. Substitution
5. Complete Combustion
6. Incomplete Combustion
Now: Hydrocarbon Derivative Reactions Types
7. Elimination
8. Esterification
Type 7 : Elimination
-Elimination reactions take place between organic halides (R - X) and alcohols(R -
OH).
-It is the opposite of an addition reaction in that alkenes and alkynes are the
products when X and OH are removed from the organic halides or alcohols.
Two Subtypes:
-Organic Halide Elimination
-Alcohol Elimination
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Sub-Type 1: Organic Halide Elimination
General Equation
R - X + OH- —> R + HOH + X
-
organic halide alkene halogen ion
alkyne
Example 1: Elimination of 2-bromopropane
Example 2: Elimination of 3-iodohexane
Sub-Type 2: Alcohol Elimination
-alcohol elimination reactions requires a catalyst (ex: sulfuric acid)
General Equation
R - OH ------> R + HOH alcohol acid alkene
alkyne
Example 1: Elimination of ethanol
Example 2: Elimination of 3-pentanol
Chemistry 2202
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Questions: Complete the following chart. Name: ____________________
1. Write elimination reactions for each of the following organic halides.
1. 3-chlorohexane
2. 2-bromobutane
3. 4-iodononane
2. Write elimination reactions for each of the following alcohols.
1. 1-butanol
2. 3-hexanol
3. 2-pentanol
3. Complete the following elimination reactions using structural formulas.
1.
2-pentanol ---->
2. 3-chloroheptane + hydroxide ion
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Type 8: Esterfication
-Esterfication reactions take place between organic(carboxyl) acids and alcohols.
-The result is the formation of an ester and water
-The hydroxyl group from the organic acid joins with the hydrogen atom from the
alcohol to form a water molecule.
General Equation
Organic Acid + Alcohol ------> Ester + Water
Example 1: methanoic acid + ethanol
Example 2: propanoic acid + 1-pentanol
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Chemistry 2202
Questions: Complete the following chart. Name: ____________________
1. Write esterfication reactions for each of the following.
1. methanoic acid + methanol
2. propanoic acid + 1-ethanol
3. butanoic acid + 2-butanol
4. ethanoic acid + 2-propanol
5. hexanoic acid + 2-butanol
2. Fill in and Name the missing reactant in each of the following esterfication reactions.
1.
2.
3.