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H2 Chemistry > 09 Intro to Organic Chemistry > Flashcards

09 Intro to Organic Chemistry Flashcards

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1
Q

Hydrocarbons

A
  1. Alkanes
    a. Functional Group: –
    b. General Formula: CnH2n+2
  2. Alkenes
    a. Functional Group: C=C
    b. General Formula: CnH2n
  3. Alkyne
    a. Functional Group: C≡C
    b. General Formula: CnH2n-2
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2
Q

Halogen Derivatives

eg. CFCs

A
  1. Halogenalkane
    a. Functional Group: –X
    b. General Formula: RX
  2. Halogenarene
    a. Functional Group: ⏣-X
    b. General Formula: –

X = Cl, Br, I

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3
Q

Hydroxy Compounds

A
  1. Alcohol
    a. Functional Group: -OH
    b. General Formula: R-OH
  2. Phenol
    a. Functional Group: ⏣-OH
    b. General Formula: –
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4
Q

Carbonyl Compounds

A
  1. Aldehyde
    a. Functional Group: C=O with H as one substituent
    b. General Formula: R-C=O-H
  2. Ketone
    a. Functional Group: C=O
    b. General Formula: R-C=O-R’

R & R’ = alkyl groups of general formula CnH2n+1

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5
Q

Carboxylic Acids & Derivatives

A
  1. Carboxylic Acid
    a. Functional Group: C=OOH
    b. General Formula: R-C=OOH
  2. Ester
    a. Functional Group: C=OO
    b. General Formula R-C=OOR’
  3. Acyl Halide
    a. Functional Group: C=OX
    b. General Formula: R-C=OX
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6
Q

Nitrogen Compounds

A
  1. Amine
    a. Functional Group: NH2
    b. General Formula: R-NH2
  2. Amide
    a. Functional Group: C=O-NH2
    b. General Formula: R-C=O-NH2
  3. Amino Acid
    a. Functional Group: NH2-CH-C=OOH
    b. General Formula: NH2-CHR-C=OOH
  4. Nitrile
    a. Functional Group: C≡N
    b. General Formula: R-C≡N
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7
Q

Representation of Organic Compounds

Empirical

A

Characteristic(s):
shows simplest ratio of different atoms in a molecule

Example(s):
1. Ethane
CH3
2. Ethanoic Acid
CH2O
3. Cyclopentane-carbaldehyde
C6H10O

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8
Q

Representation of Organic Molecules

Molecular

A

Characteristic(s):
1. shows actual number of different atoms in a molecule
2. is an integral multiple, n, of empirical formula

Example(s):
1. Ethane
(CH3)2 = C2H6
2. Ethanoic Acid
(CH2O)2 = C2H4O2
3. Cyclopentane-carbaldehyde
C6H10O

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9
Q

Representation of Organic Compounds

Structural - Displayed

A

Characteristic(s):
1. shows how every atom is bonded to other atoms and the number of bonds between them
2. C & H in Benzene is not shown

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10
Q

Representation of Organic Compounds

Structural - Condensed

A

Characteristic(s):
1. shows how groups of atoms are sequentially arranged
2. bond lines omitted except for those connected to rings
3. read from left to right
4. parentheses used to denote similar groups bonded to the same atoms

Example(s):
1. Ethane
CH3CH3
2. Ethanoic Acid
CH3CO2H
3. Cyclopentane-carbaldehyde
⬠-CHO

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11
Q

Representation of Organic Compounds

Structural - Skeletal

A

Characteristic(s):
1. shows C skeleton with any functional group(s)
2. straight lines present C-C bond
3. C atom found at the junction of any 2 lines and end of any line
4. H attached to C not shown
5. Number of H attached to C is inferred from the fact that C must form 4 bonds

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12
Q

Drawing Skeletal Structures

A
  1. Straight-chain compounds are drawn in a zig-zag format
  2. When drawing single bonds, direction is irrelevant
  3. When drawing double bonds or branched chains, draw the bonds as far apart as possible
  4. Double bonds are denoted by double lines while triple bonds are denoted by triple lines
  5. All heteroatoms i.e atoms other than C and H are drawn
  6. H atoms attached to heteroatoms are drawn as well

For point 4, triple bonds are drawn in a linear fashion as it involves sp-hybridised C atoms which have a linear molecular shape.

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13
Q

Representation of Organic Compounds

Structural - Stereochemical

A

Characteristic(s):
1. shows spatial 3D structure of molecule
2. solid lines denote bonds on the same plane as the paper
3. dash lines denote bonds going into the paper
4. wedge lines denote bonds going out of the paper

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14
Q

IUPAC Naming of Organic Compounds

A

Prefix(es), Root, Suffix

prefix = substituents/ side groups
root = longest C chain bearing the principal functional group
suffix = principal functional group

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15
Q

Suffix

by priority

A
  1. Carboxylic Acid
  2. Ester
  3. Acyl Halide
  4. Amide
  5. Nitrile
  6. Aldehyde
  7. Ketone
  8. Alcohol
  9. Amine

  1. Halogens are named as substituents
  2. When > 1 functional group present, functional group with higher priority is listed as the suffix and the rest as prefix(es).
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16
Q

Root

A
  1. meth-
  2. eth-
  3. prop-
  4. but-
  5. pent-
  6. hex-
  7. hept-
  8. oct-
  9. non-
  10. dec-
17
Q

Prefix

A
  1. C≡N: cyano-
  2. C=O: oxo-
  3. -OH: hydroxy-
  4. -NH2: amino-
  5. -OR: alkoxy-
  6. -NO2: nitro-
  7. -⏣: phenyl-
18
Q

Isomerism

A
  1. Constitutional
    a. Chain
    b. Positional
    c. Functional Group
  2. Stereoisomerism
    a. Cis-trans:
    “Cis”: 2 identical groups on the same side
    “Trans”: 2 identical groups on the opposite side
    b. Enantiomerism
19
Q

Cis-trans Isomerism

Conditions

A
  1. Restricted Rotation about a bond through either
    a. double bond, C=C/ C=N/ N=N
    b. ring structure
  2. 2 different groups attached to
    a. each C atom in the double bond
    b. ≥ 2 C atom in a ring
20
Q

Enantiomerism

Conditions

aka Chiral Compounds

A
  1. Non-superimposable mirror image
  2. No interal plane of symmetry
  3. ≥ 1 chiral centre

denoted by *

21
Q

Chiral Carbon

Conditions

aka Chiral Centre

A
  1. sp3-hybridised
  2. 4 different groups attached
22
Q

Number of Stereoisomers

Formula

A

2(x+y)

x = no. of chiral centres
y = no. of double bonds that cause cis-trans

23
Q

Angle of plane-polarised light

Factors

A
  1. Concentration of solvent
  2. Temperature of solvent
  3. Type of solvent
  4. Wavelength of light
  5. Path length of plane
24
Q

Meso Compounds

Conditions

A
  1. Internal plane of symmetry
  2. Superimposable mirror images
  3. ≥ 1 chiral centre
  4. optically inactive
25
Q

Organic Species

Electrophile, EP

opposite of NP

A
  1. e--deficient species
  2. attracted to e--rich regions in a molecule
  3. may possess an empty low-lying orbital to accept an e- pair

eg. HBr, Br+, NO2+

26
Q

Organic Species

Nucleophile, NP

opposite of EP

A
  1. e--rich species
  2. attracted to e--deficient regions
  3. possess at least 1 lone pair of e-/ π bond
27
Q

Organic Species

Free Radical, FR

A
  1. contains unpaired e-
  2. electrically neutral
28
Q

Organic Reactions

Substitution

A

Characteristic(s):
1. Replacement of an atom/ group of atoms by another atom/ group of atoms
2. 2 species –> 2 pdts
3. σ bond broken and reformed at the same C atom
4. Degree of unsaturation remains unchanged
5. Hybridisation of C remains unchanged

Example(s):
1. FR Substitution, FRS in Alkanes
2. EP Substitution, EPS in Arenes
3. NP Substitution, NPS in Halogenalkanes

29
Q

Organic Reactions

Addition

opposite of Elimination

A

Characteristic(s):
1. Unsaturation must be present in the molecule
2. 2 species –> 1 pdt
3. π bond broken –> 2 σ bond reformed at the 2 C atoms
4. Degree of unsaturation decreases
5. Hybridisation of C changes from sp2 to sp3

Example(s):
1. EP Addition, EPA in Alkenes
2. NP Addition, NPA in Aldehydes & Ketones

30
Q

Organic Reactions

Elimination

opposite of Addition

A

Characteristic(s):
1. Removal of atoms/ group of atoms from adjacent C atoms to form multiple bonds
2. 2 σ bonds broken –> π bond formed between 2 C atoms
3. Degree of unsaturation increases

31
Q

Organic Reactions

Condensation

A

Characteristic(s):
1. 2 molecules –> bigger molecule with the Elimination of smaller molecules such as H2O and HCl
2. Degree of unsaturation remains unchanged

32
Q

Organic Reactions

Hydrolysis

A

H2O is used to break a bond in a molecule

33
Q

Organic Reactions

Oxidation, [O]

A

Characteristic(s): Same as those of [O] rxns

34
Q

Organic Molecule

Reduction, [R]

For organic reduction reactions, [H] is accepted

A

Characteristic(s): Same as those of [R]

35
Q

Organic Reactions

Rearrangement

A

Characteristic(s):
Migration of an atom/ group of atoms from one site to another within the same molecule

36
Q

Homolytic Fission

Definition

A

The breaking of a covalent bond such that 1 e- goes to each one of the atoms, forming free radicals

Represented by half-headed arrow which indicates movement of 1 electron

37
Q

Heterolytic Fission

Definition

A

The breaking of a covalent bond such that both e- go to the same atom, typically forming cation and anions.

Represented by full-headed arrow which indicates movement of 2 electrons

H2 Chemistry (14 decks)

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