Organic Chemistry Flashcards
C-C
Alkanes
C=C
Alkenes
C≡C
Alkynes
R-OH
Alcohol
R-O-R
Ether
R-NH2
Amine
R-X
Alkyl halide
What is it
▪️Headways overlap
▪️Stronger
▪️First bond
▪️Formed by s or sp orbitals
Sigma (σ)
What is it
▪️Sideways overlap
▪️Weaker
▪️Anything after sigma
▪️Formed by p orbitals ONLY
Pi (π)
What hybridization is stated below:
▪️1s; 3p
▪️4 sp3 orbitals
▪️4 sigma
▪️Tetrahedral
▪️109.5
▪️single bond (-)
sp3
What hybridization is stated below:
▪️1s; 2p
▪️3 sp2 orbitals (1 p orbital unhybridized)
▪️3 sigma; 1pi
▪️Trigonal Planar
▪️120
▪️double bond (=)
sp2
What hybridization is stated below:
▪️1s; 1p
▪️2 sp orbitals (2 p orbitals
unhybridized)
▪️2 sigma; 1 pi
▪️Linear
▪️180
▪️triple bond (≡)
sp
Who invented/discovered
Solid Sphere Model
John Dalton (1803)
Who invented/discovered
Plum Pudding Model
J.J. Thomson (1904)
Who invented/discovered
Nuclear Model
Ernest Rutherford (1911)
Who invented/discovered
Planetary Model
Niels Bohr (1913)
Who invented/discovered
Quantum Model
Erwin Schrodinger (1926)
Acid or Base
Bronsted-Lowry
▪️Donates p+
Acid
Acid or Base
Bronsted-Lowry
▪️Accepts p+
Base
Acid or Base
Lewis Theory
▪️e- pair acceptor
Acid
Acid or Base
Lewis Theory
▪️e- pair donor
Base
Electron withrawing
Increase Acidity
Electron Donating
Decrease Basicity; Increase acidity
What do we called?
Same connectivity
Stereo Isomer
Cis / Trans Isomers
Similar substituents on the SAME side
Cis
Cis / Trans Isomers
Similar substituents on the OPPOSITE side
Trans
What is it
▪️For prioritization in E/Z and optical isomers
▪️Based on atomic number of the first attached atom
▪️The higher the atomic number means higher priority
Cahn-Ingold Prelog (CIP) Rules
Mirror image not superimposable on itself
Chiral
Molecule and mirror image are identical
Achiral
Mirror images; have opposite configurations at all stereogenic centers
Enantiomers
Stereoisomers but not mirror images; have the same configuration at one or more centres
Diastereomers
What is it
▪️aka Paraffins
▪️Saturated
▪️Formula: CnH2n+2
▪️Tetrahedral geometry
Alkanes
What is it
▪️aka Olefins
▪️Unsaturated
▪️Formula: CnH2n
▪️Planar geometry
Alkenes
What is it
▪️aka Acetylenes
▪️Unsaturated
▪️Formula: CnH2n-2
▪️Linear geometry
Alkynes
Is an alkene nucleophilic or electrophilic?
Nucleophilic
What sp hybridized are the ff:
- Alkanes
- Alkenes
- Alkynes
- sp3
- sp2
- sp
Halogenation requires organic solvent like
- CCI4 - carbon tetrachloride
- DCM - dichloromethane
Hydrogenation requires catalyst like
- Pd - palladium
- PtO2 - platinum dioxide
Hydrogenation produces (1) which also known as (2)
- Alkane
- Reduction
Hydrohalogenation is usually done with what solvent
Ether
Aromaticity Classification
▪️Cyclic: Yes
▪️Planar: Yes all sp2
▪️Huckel’s Rule: 4n+2 pi electrons = whole number
Aromatic
Aromaticity Classification
▪️Cyclic: Yes
▪️Planar: Yes
▪️Huckel’s Rule: 4n pi electrons
Anti-aromatic
Aromaticity Classification
▪️Cyclic: No
▪️Planar: No
▪️Huckel’s Rule: Doesn’t matter
Non-aromatic (aka Aliphatic)
Most stable
Chair
Arrange the ff. to more stable to least stable
1°, 2°, 3°, methyl cation
(more stable) 3°, 2°, 1°, methyl cation (least stable)
What rule is stated below:
▪️the rich gets richer
▪️H adds to the C w/ greater no. H (less subst. C)
▪️X adds to the C w/ lesser no. H (more subst. C)
Markovnikov’s Rule
What are the criteria for Aromaticity
- Cyclic
- Flat/Planar = sp2 (trigonal planar)
- Conjugates double bonds (alternating)
- Huckel’s Rule: 4n+2=πe-
(where n=0,1,2,3…integer)
o First organic compound synthesized from inorganic matter
o Final waste product of protein metabolism
o Discovered by Friedrich Wohler (1828) from heating lead cyanate and ammonia
Urea
Parent ring for anthraquinone glycosides
Anthracene
Another name for Aniline
Aminobenzene
Another name for Toluene
Methylbenzene
▪ Discovered by Joseph Lister (Father of Antisepsis)
▪ First antiseptic agent
▪ Phenol Coefficient – ↑PC ↑ antiseptic activity
Phenol/Carboxylic Acid or aka Hydroxybenzene
aka hydroxytoluene; Lysol®
Cresol
Dextrorotatory (d / +) movement
Right (clockwise)
Levorotatory (l / -) movement
Left (counterclockwise)
• Duality of the atom to flex or bend due to:
✓ Rotation along a single bond (acyclic or open chain)
✓ Torsional strain (Cyclic)
Conformational Isomers
Compounds that exhibit optical activity (ability of a compound to rotate plane polarized light either to the left or right)
Configurational Isomers
- C2 epimer of D-glucose
- C4 epimer of D-glucose
- D-mannose
- D-galactose
OH pointing downward
Alpha
OH pointing upward
Beta
What ointment is this?
Benzoic Acid + Salicylic Acid
Whitfield’s Ointment
used in suntan lotions to prevent the dangerous UV rays from reaching the skin
PARA-AMINOBENZOIC ACID
Same Proton (p+), atomic #, element
Different in atomic mass
IsotoPes
Same Bigat (atomic weight) Protons & Neutrons
Differ in elements
IsoBars
Same Neutron
Differ in elements
IsotoNes
Same molecular formula
Differ in structure
IsoMers
Same type
Same order of atoms
Different spatial arrangement
Different configuration
Stereoisomers
Isomers that differ in spatial arrangement of atoms, rather than order of atomic connectivity
Stereoisomers
Stereoisomers that mirror images, but NOT superimposable
Enantiomers
Not mirror images and not superimposable
Diasteriomers