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Chemistry Sem 2 > Introduction to organic chemistry > Flashcards

Introduction to organic chemistry Flashcards

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1
Q

Classification of organic compounds/hydrocarbons (3)

A
  1. Aliphatic → open chains
  2. Acyclic → closed ring
  3. Aromatic → contain benzene ring
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2
Q

Functional group

A

Atom/group of atoms within the organic compound that is responsible for its characteristic chemical properties

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3
Q

Homologous series

A
  • Family of compounds having the same functional group
  • Represented by general formula
  • Differs from successive member by -CH₂- group (methylene)
  • Similar chemical properties
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4
Q

Classes of compounds (6)

A
  1. Hydrocarbons
  2. Halogen derivatives
  3. Hydroxyl compounds
  4. Carbonyl compounds
  5. Carboxylic acids and derivatives
  6. Nitrogen compounds
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5
Q

Hydrocarbons (3)

A
  1. Alkanes → saturated
  2. Alkene → double bond
  3. Alkyne → triple bond
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6
Q

Halogen derivatives (2)

A
  1. Halogenoalkane → e.g. chloroethane

2. Halogenoarene → benzene ring → e.g. chlorobenzene

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7
Q

Hydroxyl compounds (2)

A
  1. Alcohol → e.g. ethanol

2. Phenol → benzene ring

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8
Q

Carbonyl compounds (2)

A

C=O

  1. Aldehyde → at the end → e.g. ethanal
  2. Ketone → in the middle → e.g. propanone
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9
Q

Carboxylic acids and derivatives (3)

A
  1. Carboxylic acid → COOH → e.g. ethanoic acid
  2. Ester → e.g. methyl ethanoate
  3. Acyl halide/acid halide → COX → e.g. propanoyl chloride
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10
Q

Nitrogen compounds

A
  1. Amine → NH₂ → e.g. ethylamine
  2. Amide → CONH₂ → e.g. propanamide
  3. Amino acid → H₂NCHRCOOH
  4. Nitrile → C≡N → e.g. propanenitrile
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11
Q

Formulae of Organic Compounds (3)

A
  1. Empirical formula → simplest ratio
  2. Molecular formula → actual number
  3. Structural formula
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12
Q

Structural formula (4)

A
  1. Condensed → sequential arrangement (CH₃CH₃)
  2. Displayed/full → bonds between atoms except rings
  3. Stereochemical → spatial structure
  4. Skeletal → no show C and H
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13
Q

IUPAC Nomenclature

A
  1. Prefix(es) → side groups → alphabetical order
  2. Root → longest continuous carbon chain
  3. Suffix → principal functional group
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14
Q

Root

A
  1. meth-
  2. eth-
  3. prop-
  4. but-
  5. pent-
  6. hex-
  7. hept-
  8. oct-
  9. non-
  10. dec-
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15
Q

Suffix

A
  1. Carboxylic acid → -oic acid
  2. Ester → -yl … oate
  3. Acyl halide → -oyl halide
  4. Amide → -amide
  5. Nitrile → -nitrile
  6. Aldehyde → -al
  7. Ketone → -one
  8. Alcohol → -ol
  9. Amine → -amine
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16
Q

Prefix

A

Screw this

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17
Q

Mechanisms

A
  • Organic reactions involve breaking and forming of covalent bonds
  • Illustrate flow of e⁻ density from e⁻-rich to e⁻-deficient sites
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18
Q

Types of bond fission/cleavage (breaking) (2)

A
  1. Homolytic fission

2. Heterolytic fission

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19
Q

Homolytic fission

A
  • 1 e⁻ goes to each atom

- Forms free radicals

20
Q

Heterolytic fission

A
  • Both e⁻ go to same atom
  • Forms + and - ions
  • Both go to leaving group → when C less electronegative than X → carbocation
  • Both go to carbon → when C more electronegative than X → carbanion
21
Q

Degree of substitution

A
  • Number of alkyl or aryl groups bonded to it

- Primary, secondary, tertiary, quaternary

22
Q

Types of organic species (attacking) (3)

A
  1. Electrophile
  2. Nucleophile
  3. Free radical
23
Q

Electrophile

A
  • e⁻ pair acceptor (subset of Lewis acids)
  • e⁻-deficient
  • Attracted to regions of negative charge/e⁻-rich sites in a molecule
  • May possess empty low-lying orbitals
24
Q

Nucleophile

A
  • e⁻ pair donor (subset of Lewis base)
  • e⁻-rich
  • Attracted to regions of negative charge/e⁻-deficient sites in a molecule
  • Possess at least 1 lone pair of e⁻
25
Q

Free radical

A
  • Contains unpaired e⁻ formed from homolytic fission

- Electrically neutral

26
Q

Types of organic reactions

A
  1. Addition → when there is unsaturation
  2. Substitution
  3. Elimination → removal from adjacent Cs → multiple bonds
  4. Hydrolysis
  5. Condensation
  6. Oxidation
  7. Reduction
  8. Rearrangement
27
Q

Isomerism

A

Existence of ≥ 2 compounds with the same molecular formula but with different arrangement of the atoms

28
Q

Types of isomerism (2)

A
  1. Constitutional isomerism

2. Stereoisomerism

29
Q

Constitutional isomerism

A

Same molecular formula but different structural formula

30
Q

Types of constitutional isomerism (3)

A
  1. Chain isomers → straight vs branched
  2. Positional isomers → diff position of functional group
  3. Functional group isomers → diff functional groups
31
Q

Stereoisomerism

A

Same molecular formula but different spatial arrangement of atoms

32
Q

Types of stereoisomerism (2)

A
  1. Cis-trans isomerism

2. Enantiomerism

33
Q

Cis-trans isomerism

A
  1. Restricted rotation about a double bond or a bond in a ring structure
  2. Double bond with two different groups attached to each of the two atoms in the double bond or a ring structure with two different groups attached to two atoms in the ring structure
  • Maximum number of isomers = 2^n where n is no. of C=C bonds
34
Q

Cis

A

Same side

35
Q

Trans

A

Opposite sides

36
Q

Properties of cis-trans isomers

A
  • Generally have similar chemical properties

- Different physical properties (could be because of polarity/fitting into a crystalline lattice)

37
Q

Enantiomerism

A

If it forms a non-superimposable mirror image → chiral compounds

38
Q

Chiral compounds

A
  • Do not have a plane of symmetry

- Usually contains one or more chiral centres

39
Q

Chiral carbon

A
  • sp³ hybridised

- 4 different groups attached to it

40
Q

Rotation of plane-polarised light and optical activity

A

Enantiomers rotate plane-polarised light in different directions (clockwise/anti-clockwise) → optically active

41
Q

Plane-polarised light

A

Light-wave vibrates along same plane

42
Q

Racemic mixture

A

Equal proportion of enantiomers → not optically active

43
Q

Molecules with > 1 chiral centres

A

Generally, a molecule with n chiral centers → maximum of 2^n stereoisomers

44
Q

Diastereomers

A

Stereoisomers which are not mirror images of each other

45
Q

Meso compound

A

> 1 chiral centre but has a plane of symmetry → mirror images that are superimposable → optically inactive

Chemistry Sem 2 (5 decks)

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