Functional grps Flashcards
(88 cards)
1
Q
Free radical substitution (SR)
A
General reaction mechanism of alkanes
2
Q
Electrophilic addition (AE)
A
General reaction mechanism of alkenes and alkynes
3
Q
Electrophilic substitution (SE)
A
General reaction mechanism of aromatics
4
Q
Nucleophilic substitution (SN)
A
General reaction mechanism of alkyl halides and alcohols
5
Q
Nucleophilic addition (AN)
A
General reaction mechanism of Carbonyl compounds (aldehydes and ketones)
6
Q
Nucleophilic acyl substitution (SNAcyl)
A
General reaction mechanism of carboxylic acids and their derivatives
7
Q
Redox
A
General reaction mechanism of alcohols, carbonyl compounds, and carboxylic acids
8
Q
Reactions undergone:
1. Complete Combustion
2. Incomplete Combustion
3. Free radical Substitution (SR)
A
Alkane
9
Q
- Sufficient oxygen is present
- Reagent: sufficient O2
- Catalyst: heat
- Products: CO2 and H2O
(alkane)
A
Complete combustion
10
Q
- Insufficient oxygen is present
- Reagent: limited O2
- Catalyst: heat
- Products: CO and H2O
(alkane)
A
Incomplete combustion (alkane)
11
Q
- Small reacting molecule replaces an atom or a group of atoms on a hydrocarbon or hydrocarbon derivative
- It is also known as ALKANE HALOGENATION because the “free radical” is derived from a halogen molecule.
A
Free-radical substitution
12
Q
- Reagent: X2
o Catalyst: Presence of UV light
o Product: alkyl halide
A
Free-radical substitution
13
Q
Reactions undergone:
1.Combustion
a. Complete Combustion
b. Incomplete Combustion
- Electrophilic Addition (AE)
a. Symmetrical
b. Asymmetrical
A
Alkene
14
Q
Symmetrical electrophilic addition
A
i. Hydrogenation
ii. Halogenation
15
Q
Asymmetrical electrophilic addition
A
i. Hydrohalogenation
ii. Hydration
16
Q
- It is also known as reductive/catalytic hydrogenation.
*Hydrogen atom is added to each carbon atom of a double bond
A
HYDROGENATION
17
Q
- Reagent: H2
- Catalyst: Pt, Pd, Ni
- Product: double bond becomes a single bond
A
Hydrogenation
18
Q
Halogen atom is added to each carbon atom of a double bond
A
Halogenation
19
Q
- Reagent: X2
- Catalyst: DCM (dichloromethane)
- Product: Alkyl dihalide (or vicinal dihalide)
A
Halogenation
20
Q
- Hydrogen halide (HCl, HBr, or HI) is incorporated into molecules of an organic compound
o follows Markovnikov’s Rule
A
HYDROHALOGENATION
21
Q
- Reagent: HX
- Catalyst: ether
- Product: Alkyl halide
A
Hydrohalogenation
22
Q
- aka acid-catalyzed hydration
- H2O is incorporated into molecules of an organic compound
o follows Markovnikov’s Rule
A
Hydration
23
Q
- Reagent: H2O
- Catalyst: H2SO4 or H+
o sometimes the reagent and catalyst are combined together and written as H3O+ - Product: Alcohol
A
Hydration
24
Q
This rule is applied to asymmetrical addition reactions of alkenes and alkynes (i.e., in hydrohalogenation and hydration reactions)
A
THE MARKOVNIKOV’S RULE
25
states that when an asymmetrical molecule of the form HQ adds to an asymmetrical alkene, the hydrogen atom from the HQ becomes attached to the unsaturated carbon atom that already has the most hydrogen atoms.
THE MARKOVNIKOV’S RULE
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Reactions undergone:
1. Combustion
2. Electrophilic Addition (AE)
Alkyne
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i. Partial Hydrogenation
ii. Complete Hydrogenation
iii. Partial Halogenation
iv. Complete Halogenation
Symmetrical electrophilic addition
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i. Partial Hydrohalogenation
ii. Complete Hydrohalogenation
iii. Hydration
Asymmetrical electrophilic addition
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* Hydrogen atom is added to each carbon atom of a triple bond
* Reagent: 1 mole of H2
* Catalyst: Lindlar’s Catalyst
- Product: triple bond becomes a double bond
Partial hydrogenation
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is a heterogeneous catalyst consisting of palladium (Pd) deposited on calcium carbonate or barium sulfate.
Lindlar’s Catalyst
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* 2 molecules of Hydrogen are added to each carbon atom of a triple bond
complete hydrogenation
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* Reagent: 2 moles of H2
* Catalyst: Pt/Pd/Ni
* Product: triple bond becomes a single bond
Complete hydrogenation
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* Halogen atom is added to each carbon atom of a triple bond
* Reagent: 1 mole of X2
* Catalyst: DCM
* Product: alkene dihalide (vicinal dihalide)
Partial Halogenation
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* Halogen atom is added to each carbon atom of a triple bond
* Reagent: 2 moles of X2
* Catalyst: DCM
* Product: alkyl tetrahalide
Complete halogenation
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* 1 molecule of hydrogen halide (HCl, HBr, or HI) is incorporated into molecules of an organic compound
o follows Markovnikov’s Rule
Partial hydroghalogenation
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* Reagent: 1 mole of HX
* Catalyst: ether
* Product: Alkene halide (vinyl halide)
PARTIAL HYDROHALOGENATION
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* 2 molecules of hydrogen halide (HCl, HBr, or HI) is incorporated into molecules of an organic compound
o follows Markovnikov’s Rule
* Reagent: 2 moles of HX
* Catalyst: ether
* Product: Alkyl dihalide (or geminal dihalide)
Complete hydrohalogenation
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* aka acid-catalyzed hydration
* H2O is incorporated into molecules of an organic compound
o follows Markovnikov’s Rule
* Reagent: H2O
* Catalyst: H2SO4 , HgSO4
* Product: enol (which can undergo keto-enol tautomerism)
Hydration (alkyne)
39
Reactions undergone:
1.Electrophilic Substitution (SE)
Arene (aromatics)
40
Under Electrophilic Substitution (SE)
a. Halogenation
b. Sulfonation
c. Nitration
d. Complete reduction of Benzene
e. Friedel-Crafts Alkylation
f. Friedel-Crafts Acylation
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* A hydrogen atom on a benzene ring can be replaced by bromine or chlorine if benzene is treated with a halogen (usually Br2 or Cl2) in the presence of a catalyst
Halogenation (arene)
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* Reactant: Br2 or Cl2
* Catalyst: FeBr3, FeCl3 , AlBr3, AlCl3
* Product: halobenzene
Halogenation (arene)
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* A hydrogen atom on a benzene ring can be replaced by sulfonic acid if benzene is treated with SO3 in the presence of fuming sulfuric acid
SULFONATION
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- Reactant: concentrated H2SO4 or SO3
* Catalyst: fuming H2SO4
* Product: benzenesulfonic acid
Sulfonation
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* A hydrogen atom on a benzene ring can be replaced by a nitro group if benzene is treated with HNO3 in the presence of sulfuric acid.
Nitration
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* Reactant: conc. HNO3
* Catalyst: conc. H2SO4
* Product: nitrobenzene
Nitration
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* 3 H2 molecules are added into the benzene ring to completely remove all the double bonds.
Complete reduction of benzene
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* Reactant: 3 H2
* Catalyst: Pt/Pd/Ni + heat
* Product: cyclohexane
Complete reduction of benzene
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- An alkyl group (R–) from an alkyl chloride (R–Cl) substitutes for a hydrogen atom on the benzene ring.
* Alkylation is the most important industrial reaction of benzene.
FRIEDEL-CRAFTS ALKYLATION
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* Reactant: alkyl halide
* Catalyst: AlCl3
* Product: alkylbenzene
FRIEDEL-CRAFTS ALKYLATION
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* An acyl group (RC=O–) from an acyl chloride (RC=OCl) substitutes for a hydrogen atom on the benzene ring.
FRIEDEL-CRAFTS ACYLATION
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* Reactant: acyl halide
* Catalyst: AlCl3
* Product: acylbenzene
FRIEDEL-CRAFTS ACYLATION
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Reactions undergone:
1. Nucleophilic substitution (SN)
2. Oxidation
3. Dehydration
Alcohol
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Alcohol halogenation with:
i. with PBr3
ii. with SOCl2
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* A bromine atom is substituted for the hydroxyl group
* Reagent: PBr3
* Catalyst: Ether
* Product: Alkyl bromide
HALOGENATION WITH PHOSPHORUS TRIBROMIDE
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* A chlorine atom is substituted for the hydroxyl group
* Reagent: SOCl2
* Catalyst: pyridine
* Product: Alkyl chloride
HALOGENATION WITH THIONYL CHLORIDE
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* Reagent: Mild oxidizing agent
* Catalyst: N/A
* Product: aldehyde
PARTIAL OXIDATION OF PRIMARY ALCOHOL
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* Reagent: Strong oxidizing agent
* Catalyst: N/A
* Product: carboxylic acid
FULL OXIDATION OF PRIMARY ALCOHOL
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* Reagent: Either a mild or strong oxidizing agent
* Catalyst: N/A
* Product: ketone
OXIDATION OF SECONDARY ALCOHOL
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* Reaction in which water is formed from the removal of the components of water (H and OH) from a single reactant
* This is an example of an ELIMINATION reaction.
o follows Zaitsev’s Rule
DEHYDRATION
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* Reagent: Sulfuric acid (H2SO4)
* Catalyst: Heat; likely at higher temperatures (~180°C)
* Product: alkene
DEHYDRATION
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Mild/weak oxidizing agents
o PCC (pyridinium chlorochromate)
o PDC (pyridinium dichromate)
o Periodinane
o Swern
o DMP (Dess-Martin)
63
Strong OA
o KMnO4 (potassium permanganate)
o K2Cr2O7 (potassium dichromate)
o H2CrO4 (chromic acid)
64
Mild/weak RA
NaBH4
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Strong RA
LiAlH4
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- a rule that carries the name of the Russian chemist
- major product is the alkene that has the greatest number of alkyl groups attached to the carbon atoms of the double bond.
Zaitsev’s rule
67
Reactions undergone:
1. NUCLEOPHILIC ADDITION (AN)
2. NUCLEOPHILIC ADDITION + ELIMINATION (ANE)
3. REDOX
Aldehyde or Ketone
68
Under NUCLEOPHILIC ADDITION (AN) (Aldehyde or Ketone)
a. Hydration
b. Addition of 1 mole of alcohol
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Under NUCLEOPHILIC ADDITION + ELIMINATION (ANE) (Aldehyde or Ketone)
a. Addition of two moles of alcohol
b. Addition of ammonia/primary amine
c. Grignard reaction (RMgX)
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* Reagent: H2O
* Catalyst: H2SO4, H3O+, or OH-
* Product: Gem diol (hydrate)
Hydration
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* Reagent: 1 mole of alcohol (ROH)
* Catalyst: H2SO4, H3O+, or H+
* Product: hemiacetal or hemiketal
ADDITIONAL OF 1 MOLE OF ALCOHOL
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* Reagent: 2 moles of alcohol (ROH)
o or just add another 1 mole of alcohol to the hemiacetal formed
* Catalyst: H2SO4, H3O+, or H+
* Product: acetal or ketal
ADDITION OF 2 MOLES OF ALCOHOL
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* The reaction of aldehydes and ketones with ammonia or 1º-amines forms imine derivatives, also known as Schiff bases (compounds having a C=N function).
ADDITION OF AMMONIA/PRIMARY AMINE
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* Reagent: NH3 or RNH (primary amine)
* Catalyst: H2SO4, H3O+, or H+
* Product: Imine (or Schiff base)
ADDITION OF AMMONIA/PRIMARY AMINE
75
* Reagent: Grignard Reagent (RMgX)
o R = an alkyl group
o Mg = magnesium
o X = a halogen
* Catalyst: Ether and Hydrogen ion/Hydronium ion (H3O+)
* Product: Secondary alcohol (aldehyde); tertiary alcohol (ketone)
GRIGNARD REACTION (using RMgX reagent)
76
* Reagent: Either a mild or strong reducing agent
* Catalyst: N/A
* Product: primary alcohol
REDUCTION OF ALDEHYDE
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* Reagent: Either a mild or strong reducing agent
* Catalyst: N/A
* Product: secondary alcohol
REDUCTION OF KETONE
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* Reagent: Either a mild or strong oxidizing agent
* Catalyst: N/A
* Product: carboxylic acid
OXIDATION OF ALDEHYDE
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Reactions undergone:
1. NUCLEOPHILIC SUBSTITUTION (SNAcyl)
2. REDOX
a. Partial reduction
b. Full reduction
Carboxylic acid
80
Under NUCLEOPHILIC SUBSTITUTION (SNAcyl)
a. Fischer Esterification
b. Ammonolysis
c. Aminolysis
d. Acyl halide formation
e. Hydrolysis of any carboxylic acid derivative
81
* An esterification reaction is the condensation reaction of a carboxylic acid with an alcohol (or a phenol) to produce an ester.
FISCHER ESTERIFICATION
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* Reagent: Alcohol
* Catalyst: H2SO4, H+, or H3O+
* Product: Ester
FISCHER ESTERIFICATION
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* Reagent: Ammonia (NH3)
* Catalyst: Heat
* Product: Amide
AMMONOLYSIS
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* Reagent: primary or secondary amine
* Catalyst: Heat
* Product: Amide
AMINOLYSIS
85
* Reagent: SOCl2 (thionyl chloride)
* Catalyst: Use an acid catalyst if reactant is ester; DCC if reactant is an amide
* Product: Acyl chloride
ACYL HALIDE FORMATION
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* Reagent: H2O
* Catalyst: H2SO4 or H+
o sometimes the reagent and catalyst are combined together and written as H3O+
- Product: Carboxylic acid
HYDROLYSIS OF ANY CARBOXYLIC ACID DERIVATIVE
87
* Reagent: weak reducing agent
* Catalyst: N/A
* Product: aldehyde
PARTIAL REDUCTION OF CARBOXYLIC ACID AND DERIVATIVES
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* Reagent: strong reducing agent
* Catalyst: N/A
* Product: primary alcohol
FULL REDUCTION OF CARBOXYLIC ACID AND DERIVATIVES
