Chemistry Unit #5: Organic Chemistry Topics Test on Friday, February 10, 2017 Flashcards
Test
…………………………………….O
Cr₂O₇²⁻/H⁺………………….||
Primary alcohol ===> CH₃ - CH₂ - CH₂ - OH =========> CH₃ - CH₂ - CH
………………………………………………………………………………………………(aldehyde)
Compare and contrast catalytic cracking to catalytic reforming.
Similarities
They both need catalysts
Used to make fuels
Oxygen cannot be present
Differences Catalytic cracking makes smaller chains from larger ones while catalytic reforming produces longer chains from smaller ones
What does orange turn into when Alcohol is warmed with Cr₂O₇²⁻/H⁺ (acidified potassium dichromate)? It is the basis behind the breathalyser test.
Orange will turn to green
What is the name and reduced formula of this structural formula?
CH₃ — CH₂ — CH₂ — CH₃
C₄H₁₀ and butane
What is the Catalyst for the Oxidation of Alcohols?
Cr₂O₇²⁻/H⁺ (acidified potassium dichromate)
What forms from the Oxidation of Primary Alcohols?
Aldehydes
What chemical process may be used to convert the petroleum distillation residue into gasoline?
Catalytic cracking
What are the 4 Alkene Addition Reaction
1.) Halogens: (F₂, Cl₂, Br₂, I₂)
CH₃ — CH = CH₂ + Br₂ ===> CH₃ — CHBr — CH₂Br
2.) Hydrogen gas, H₂ (Turns it into alkane)
CH₂ = CH₂ + H₂ ===> CH₃ — CH₃
3.) Water, H₂O (Makes an alcohol)
CH₃ — CH = CH₂ + HOH ===> CH₃ — CH₂ — CH₂OH
4.) Hydrogen halides; (HF, GCl, HBr, HI)
CH₃ — CH = CH — CH₃ + HBr ===> CH₃ - CHBr — CH₂— CH₃
What forms from the Oxidation of Secondary Alcohols?
Ketones
What is the name and reduced formula of this structural formula?
CH₃ — CH₂ — CH₂ — CH₂ — CH₂ — CH₃
C₆H₁₄ and hexane
How does the average number of carbon atoms per molecule vary for the fractionation product location shown in figure H2. Explain this order using IMF. (2)
As the number of carbons on the chains increase, they are distilled lower in the tower.
This occurs because the longer chains have more IMF, resulting in higher boiling points
What forms from the Oxidation of Tertiary Alcohols?
Tertiary Alcohols cannot undergo this reaction
What is the product of this Nucleophilic Substitution of Halogenalkanes?
CH₃
| CH₃ - C - CH₃ + OH⁻ ===>
|
Cl
CH₃
|
CH₃ - C - CH₃ + Cl⁻
|
OHWhat is the name and reduced formula of this structural formula?
CH₃ — CH₂ — CH₂ — CH₂ — CH₃
C₅H₁₂ and pentane
What physical property is used to separate different compounds in a petroleum fractionation tower?
Boiling point
What is the name and reduced formula of this structural formula?
CH₃ — CH₂ — CH₂ — CH₂ — CH₂ — CH₂ — CH₃
C₇H₁₆ and heptane
What is the name and reduced formula of this structural formula?
CH₂ — CH₂
C₂H₆ and ethane
What is the name and reduced formula of this structural formula?
CH₃
CH₄ and methane
What is the name and reduced formula of this structural formula?
CH₃ — CH₂ — CH₂ — CH₂ — CH₂ — CH₂ — CH₂ — CH₃
C₈H₁₈ and octane
What is the name and reduced formula of this structural formula?
CH₃ — CH₂ — CH₃
C₃H₈ and propane
What is the name of this structure?
CH₃ CH₂ — CH₂ — CH₃
| |
CH₃ = C — CH — CH — CH₂ — CH₂ — CH₃
|
CH₂ — CH₃
3-ethyl-2-methyl-4-propyl-1-heptene
What are the three factors on which Boling point depends on? 3 + (3 - 4 explanations)
Polarity
Substances with hydrogen bonding have higher boiling points than those with dipole-dipole or only London Dispersion. Alkanes, alkenes, and benzne are non-polar with only London Dispersion forces Aldehydes, ketones, and esters experience the stronger dipole-dipole forces Amines, alcohols and carboxylic acids exhibit hydrogen bonding (highest Boling Point) Molar Mass Generally, higher molar mass means higher boiling points for non-polar molecules CH₄ gas at room temperature Liquid at room temperature Very long chains form waxy solids Straight vs. Branched chains Straight chains have higher boiling point Branching makes molecules more spherical, reducing contact surface area Less attraction between molecules
What are the 3 main points on Benzene?
Benzene does not undergo addition reaction, but rather substitution reactions,
Benzene does not react with KMnO₄,
Benzene’s carbon bonds are equivalent,
Therefore benzene cannot have double bonds.
What is the Polymerization of this?
CH₂ = CHCl ==============>
(Polymerization)
CH₂ = CHCl ==============> — CH₂ — CHCl —
What is the structural formula of Benzene?
The structural formula of Benzene is C₆H₆
What is the difference between Empirical, Molecular and Structural Formulas? 4
Molecular formulas tell you how many atoms of each element are in a compound,
Empirical formulas tell you the simplest or most reduced ratio of elements in a compound. If a compound's molecular formula cannot be reduced any more, then the empirical formula is the same as the molecular formula.
Structural Formula shows how the atoms are arranged
What is the functional group name for the class of Nitriles that has an ID of -C≡N
nitrile
What are Structural Isomers?
Isomers are compounds with the same molecular formula but having a different structure (arrangement of atoms)
What is the Polymerization of this?
CH₂ = CH₂ ==============>
(Polymerization)
CH₂ = CH₂ ==============> — CH₂ — CH₂ —
What is the functional group name for a Arenes that has an ID of ⬡
phenol
phenyl
What is the class name for a functional group of alkyl that has an ID of -CH₃
Alkanes
What is the reason that Alkanes are saturated compounds
It is because Alkanes consist entirely of single bonds
What is the class name for a functional group of alkenyl that has an ID of -C=C-
Alkenes
How many Structural Isomers are there for C₆H₁₄?
5
C must have 4 bonds
H must have 1 bond
O must have 2 bonds
| | | | | |
— C— C— C— C— C— C —
| | | | | |
| | | | — C— C— C— C— C— | | | | — C — |
| | | | — C— C— C— C— C— | | | | — C — |
| — C — | | | — C— C— C— C — | | | — C — |
|
— C —
| | |
— C— C— C— C —
| | |
— C —
|
How does the mechanism Termination happen for the Free Radical Mechanism for Alkane Substitution Reaction?
It happens when any two free radicals combine
What is the class name for a functional group of alkynyl that has an ID of -C≡C-
Alkynes
What is the functional group name for the class of Carboxylic Acids that has an ID of COOH
carboxyl
What is the functional group name for the class of Alkynes that has an ID of -C≡C-
alkynyl
What is the functional group name for the class of Esters that has an ID of O=C-O-C-
ester
What is the class name for a functional group of halogen that has an ID of F, Cl, Br, I
Halogenoalkanes
What homologous series are Saturated Compounds? Explain. 4
Saturated compounds are hydrocarbons that contain only single bonds between carbon atoms.
They are the simplest class of hydrocarbons. They are called saturated because each carbon atom is bonded to as many hydrogen atoms as possible. In other words, the carbon atoms are saturated with hydrogen.
What is the functional group name for the class of Amides that has an ID of O=C-N
carboxamide
How many Structural Isomers are there for C₅H₁₂?
3
C must have 4 bonds
H must have 1 bond
O must have 2 bonds
| | | | |
— C— C— C— C— C—
| | | | |
| | | | — C— C— C— C— | | | | — C — |
| — C — | | | — C— C— C— | | | — C — |
What is the functional group name for the class of Amine that has an ID of -NH₂
amine
How many Structural Isomers are there for C₂H₆O?
2
C must have 4 bonds H must have 1 bond O must have 2 bonds
H H | | H — C — C — OH | | H H
H H | | H — C — O — C — H | | H H
What is the Skeletal Formula for pentane?
Skeletal Formula for pentane: ╱╲╱╲
What class can form saturated compounds?
Alkanes
What is the functional group name for the class of Ketones that has an ID of R-CO-R
carbonyl
What does the substitution of a halogen onto an alkane require?
The substitution of a halogen onto an alkane requires UV light.
What is the functional group name for the class of Aldehydes that has an ID of HC=O
aldehyde
Why does the substitution of a halogen onto an alkane require UV light?
UV light is strong enough to split the halogen molecule into two atoms.
O
Cr₂O₇²⁻/H⁺ and heat ||
Primary alcohol ===> CH₃ — CH₂ — CH₂ — OH =================> CH₃ — CH₂ — CH
(aldehyde)
OH O
| Cr₂O₇²⁻/H⁺ and heat || Secondary alcohol ===> CH₃ — CH — CH₃ =================> CH₃ — C — CH₃
(ketones)
OH
| Cr₂O₇²⁻/H⁺ and heat Tertiary alcohol ===> CH₃ — C — CH₃ =================> NO REACTION
|
CH₃
O
Cr₂O₇²⁻/H⁺ and heat ||
Primary alcohol ===> CH₃ — CH₂ — CH₂ — OH =================> CH₃ — CH₂ — CH
(aldehyde)
OH O
| Cr₂O₇²⁻/H⁺ and heat || Secondary alcohol ===> CH₃ — CH — CH₃ =================> CH₃ — C — CH₃
(ketones)
OH
| Cr₂O₇²⁻/H⁺ and heat Tertiary alcohol ===> CH₃ — C — CH₃ =================> NO REACTION
|
CH₃
What is the functional group name for the class of Ethers that has an ID of -C-O-C-
ether
What is the Alkene general formula?
Alkene general formula: CnH₂n
What is the functional group name for the class of Alcohols that has an ID of -OH
hydroxyl
What is the catalyst of esters to make carboxylic acids?
H₂SO₄ (sulfuric acid) and heat
• Alkene Addition Reactions (4)
1.) Halogens: (F₂, Cl₂, Br₂, I₂) CH₃ — CH = CH₂ + Br₂ ===> CH₃ — CHBr — CH₂Br 2.) Hydrogen gas, H₂ (Turns it into alkane) CH₂ = CH₂ + H₂ ===> CH₃ — CH₃ 3.) Water, H₂O (Makes an alcohol) CH₃ — CH = CH₂ + HOH ===> CH₃ — CH₂ — CH₂OH 4.) Hydrogen halides; (HF, GCl, HBr, HI)
CH₃ — CH = CH — CH₃ + HBr ===> CH₃ - CHBr — CH₂— CH₃
• Alkene Addition Reactions (4)
1.) Halogens: (F₂, Cl₂, Br₂, I₂) CH₃ — CH = CH₂ + Br₂ ===> CH₃ — CHBr — CH₂Br 2.) Hydrogen gas, H₂ (Turns it into alkane) CH₂ = CH₂ + H₂ ===> CH₃ — CH₃ 3.) Water, H₂O (Makes an alcohol) CH₃ — CH = CH₂ + HOH ===> CH₃ — CH₂ — CH₂OH 4.) Hydrogen halides; (HF, GCl, HBr, HI)
CH₃ — CH = CH — CH₃ + HBr ===> CH₃ - CHBr — CH₂— CH₃
What is the functional group name for the class of Halogenoalkanes that has an ID of F, Cl, Br, I
halogen
What is the functional group name for the class of Alkane that has an ID of -CH₃
alkyl
What is the Alkane general and IHD formula?
Alkane general and IHD formula: CnH₂n₊₂
What is the functional group name for the class of Alkenes that has an ID of -C=C-
alkenyl
What is the class name for a functional group of ester that has an ID of O=C-O-C-
Esters
The smaller molecules that make up polymers are called___________.
monomers
What happens during Initiation?
Cl₂ + UV light ===>
Cl₂ + UV light ===> 2 Cl*
NOTE: The halogen forms free radical; lone electron is shown. The UV light splits the Cl gas
What is the class name for a functional group of hydroxyl that has an ID of -OH
Alcohols
What is Homolytic Fission? 4
It occurs when the shared electrons are split evenly between the bonded atoms
Atoms separate from each other and become two free radicals Contains unpaired electrons Occurs in free radical substitution of alkanes
What is the class name for a functional group of ether that has an ID of -C-O-C-
Ethers
What happens to this reaction involving a tertiary alcohol?
OH
| Cr₂O₇²⁻/H⁺ and heat Tertiary alcohol ===> CH₃ — C — CH₃ =================>
|
CH₃
There is no further reaction from the tertiary alcohol.
OH
| Cr₂O₇²⁻/H⁺ and heat
Tertiary alcohol ===> CH₃ — C — CH₃ =================> NO REACTION
|
CH₃
What happens during Propagation Part I
Cl + H — CH₃ ===>
Cl + H — CH₃ ===> CH₃ + HCl
NOTE: Free Radicals are very reactive. The chlorine free radical hooks up with the H, creating a free radical CH₃.
What is the class name for a functional group of carbonyl that has an ID of R-CO-R
Ketones
What is the formula for Determining Index of hydrogen Deficiency (IHD)?
IHD = 0.5 * [2c+2-h-x+n]
IHD = 0.5 * [2c+2-h-x+n]
The most common compound in living things is the polymer named _____.
cellulose
What is the class name for a functional group of aldehyde that has an ID of HC=O
Aldehydes
What happens during Initiation?
What happens during Propagation Part I?
What happens during Propagation Part II?
What happens during Termination?
What happens during Initiation?
Cl₂ + UV light ===>
Cl₂ + UV light ===> 2 Cl* NOTE: The halogen forms free radical; lone electron is shown. The UV light splits the Cl gas
What happens during Propagation Part I
Cl + H — CH₃ ===>
Cl + H — CH₃ ===> CH₃ + HCl NOTE: Free Radicals are very reactive. The chlorine free radical hooks up with the H, creating a free radical CH₃.
What happens during Propagation Part II
Cl₂ + *CH₃ ===>
Cl₂ + *CH₃ ===> Cl — CH₃ + Cl* NOTE: The alkyl radical reacts with a halogen molecule and reforms a halogen free radical. The CH₃ radical hooks up with the chlorine gas and creates a free radical Cl.
What happens during Termination
Cl*, *CH₃
Cl + Cl ===> Cl₂ Cl + CH₃ ===> Cl — CH₃ CH₃ + CH₃ ===> C₂H₆ NOTE: It happens when any two free radicals combine. We take all the Free radicals and mix and match. There will always be 3 products.
What happens to this reaction involving a secondary alcohol?
OH
| Cr₂O₇²⁻/H⁺ and heat Secondary alcohol ===> CH₃ — CH — CH₃ =================>
The secondary alcohol becomes a ketone. We lose the H in the OH
OH O
| Cr₂O₇²⁻/H⁺ and heat || Secondary alcohol ===> CH₃ — CH — CH₃ =================> CH₃ — C — CH₃
(ketones)
Name this organic substance.
I CH₂ — CH₂ — CH₃ O
| | || CH₃ — C — C — CH — CH₂ — CH₂ — C — OH
| | |
I I CH₂ — CH₃
4-ethyl-5,6,6-triiodo-5-propylheptanoic acid
Cellulose consists of the monomer named _____.
glucose
What is heterolytic fission? 2
It is where in both mechanisms, the halogen has a negative charge as it leaves the molecule
Both shared electrons from the covalent carbon-halogen bond went to one atom
What happens during Propagation Part II
Cl₂ + *CH₃ ===>
Cl₂ + CH₃ ===> Cl — CH₃ + Cl
NOTE: The alkyl radical reacts with a halogen molecule and reforms a halogen free radical. The CH₃ radical hooks up with the chlorine gas and creates a free radical Cl.
_____________hydrocarbon is an unsaturated hydrocarbon that is ring-shaped (cyclic) and has alternating single and double bonds between carbon atoms.
aromatic
A hydrocarbon is _____ when it has fewer hydrogen atoms than possible because it has at least one double or triple bond between carbon atoms.
unsaturated
What is the IHD of each of the following molecular formula?
C₆H₁₀
IHD = 0.5 * [2c+2-h-x+n]
IHD = 2 since (1/2)[(2 x 6) + 2 - 10] = 2
An endothermic reaction is a chemical reaction that is accompanied by or requiring the absorption of heat.
What is an endothermic reaction?
Which bond is more reactive? Double bond or single bond?
Double bond. That means that Alkenes are more reactive than Alkanes
What is the IHD of each of the following molecular formula?
C₆H₆
IHD = 0.5 * [2c+2-h-x+n]
IHD = 4 since (1/2)[(2 x 6) + 2 - 6] = 4
Name this organic substance.
CH ≡ C — CHF — CH₂ — CH₃
3-fluoro-1-pentyne
What happens to this reaction involving a primary alcohol?
Cr₂O₇²⁻/H⁺ and heat Primary alcohol ===> CH₃ — CH₂ — CH₂ — OH =================>
The primary alcohol becomes an Aldehyde. The OH at the end splits and goes to the middle
O
Cr₂O₇²⁻/H⁺ and heat || Primary alcohol ===> CH₃ — CH₂ — CH₂ — OH =================> CH₃ — CH₂ — CH
(aldehyde)
What does Br₂’s initial reddish-brown color turn into when it is oxidizing?
It becomes clear
What is an exothermic reaction?
An exothermic reaction is a chemical reaction that releases energy by light or heat. It is the opposite of an endothermic reaction. Expressed in a chemical equation: reactants → products + energy.
What is the IHD of each of the following molecular formula?
C₄H₈O
IHD = 0.5 * [2c+2-h-x+n]
IHD = 1 since (1/2)[(2 x 4) + 2 - 8] = 1
A(n)_____ is a large molecule that is made out of many smaller molecules that are joined together by covalent bonds.
polymer
What happens during Termination
Cl*, *CH₃
Cl + Cl ===> Cl₂
Cl + CH₃ ===> Cl — CH₃ CH₃ + CH₃ ===> C₂H₆ NOTE: It happens when any two free radicals combine. We take all the Free radicals and mix and match. There will always be 3 products.
Name this organic halide.
CH₃ — CH₂ — CF₂ — CHF — CHF — CH₃
2,3,4,4-tetrafluorohexane
Remember to put it in alphabetical order
What is the class name for a functional group of amine that has an ID of -NH₂
Amines
What does K₂Cr₂O₇’s initial orange color turn into when it is oxidizing?
It becomes green
Name this organic halide.
CH₃ — CH₂ — CHBr — CH₃
2-bromo-butane
Remember to put it in alphabetical order
What is the class name for a functional group of nitrile that has an ID of -C≡N
Nitriles
Name this organic substance.
CH₃ — CH₂ — CHOH — CHOH — CH₂ — CH₂ — CH₃
3,4-diheptanol
Or 3,4-butanediol
Name this organic substance.
CH₃ — CH₂ — CHOH — CHOH — CH₂ — CH₂ — CH₃
3,4-diheptanol Or 3,4-butanediol
What is the class name for a functional group of carboxyl that has an ID of COOH
Carboxylic Acids
Name this organic substance.
OH
| CH₃ — CH₂ — CH₂ — CH₂ — CH — CH₃
2-hexanol
What is the class name for a functional group of carboxamide that has an ID of O=C-N
Amides
What does KMnO₄’s initial purple color turn into when it is oxidizing?
It becomes clear
Name this organic halide.
CHBr₂— CH₂ — CH₂ — CCl = CH₂
5,5-dibromo-2-chloro-1-pentene
Remember to put it in alphabetical order
What is the IHD of each of the following molecular formula?
C₄H₉N
IHD = 0.5 * [2c+2-h-x+n]
IHD = 1 since (1/2)[(2 x 4) + 2 - 9 + 1] = 1
Rubber consists of the monomer named ethylene.
FALSE
Complete this combustion of alcohol.
CH₃ — CH₂ — CH₂ — CH₂OH + O₂ ===>
Remember that the combustion of alcohol will always make CO₂ and H₂O.
CH₃ — CH₂ — CH₂ — CH₂OH + O₂ ===> CO₂ + H₂O
Then, now you have to balance it. Start with the C's then the H's and then the O's CH₃ — CH₂ — CH₂ — CH₂OH + 6O₂ ===> 4CO₂ + 5H₂O NOTE: The only exception to balancing ever in organic chemistry is that we don't balance the oxidation of alcohols.
A _______ is one of the smallest molecules that make up a polymer.
monomer
In HCOO, the measured carbon oxygen bonds are both examples of what? 2
Resonance
Suggests that the ion doesn’t have a double and single bond but two somewhere in between
What is the class name for a functional group of phenyl that has an ID of ⬡
Arenes
What is the IHD of each of the following molecular formula? C₂Cl₂
IHD = 0.5 * [2c+2-h-x+n]
IHD = 2 since (1/2)[(2 x 2) + 2 - 2 ] = 2
Name this organic substance.
O
|| CH₃ — CH₂ — CH₂ — C — OH
Or
CH₃ — CH₂ — CH₂ — COOH
butanoic acid
Name this organic substance.
OH
|
CH₃ — CH₂ — C — CH₃
|
CH₃
2-methyl-2-butanol
Where is Aldehyde located?
C=O is at the end of the carbon chain
What forms from alcohol and carboxylic acid in the presence of heat and sulphuric acid?
An ester
When you combust an alcohol, what are the steps? 2
Write out CO₂ and H₂O.
Then, now you have to balance it. Start with the C's then the H's and then the O's
What are carboxylic acids?
They are weak organic acids that release hydrogen ions into solution.
Rubber is a synthetic carbon polymer.
FALSE
How does complete combustion happen? Is it an exothermic or endothermic reaction?
It happens when Alkanes can be a fuel, reacting with oxygen releasing heat (it is an exothermic reaction).
When you combust an alcohol, what does it produce?
CO₂ and H₂O
Complete this combustion of alcohol.
CH₃OH + O₂ ===>
Remember that the combustion of alcohol will always make CO₂ and H₂O.
CH₃OH + O₂ ===> CO₂ + H₂O
Then, now you have to balance it. Start with the C's then the H's and then the O's CH₃OH + 3/2 O₂ ===> CO₂ + 2H₂O NOTE: The only exception to balancing ever in organic chemistry is that we don't balance the oxidation of alcohols.
What organic compound that generally has a distinctive, pleasant, fruity odours that is often used in natural and artificial flavouring agents in food? (used as aromas for non-edible products
Esters
• Alcohol Esterfication
Esters are produced when carboxylic acids are heated with alcohols in the presence of an acid catalyst. The catalyst is usually concentrated sulphuric acid.
How does incomplete combustion happen? What 2 can form?
It happens when insufficient oxygen is present, the following pairs of prodicts may form along with less heat;
A.) Poisonous gas --- CO + H₂O (poison gas and water) B.) Soot --- C + H₂O (soot and water)
What is the element which life is based on Earth?
Carbon
