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Organic Chemistry > 1. Introduction to Org chem > Flashcards

1. Introduction to Org chem Flashcards

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1
Q

define homolytic fission

A

breaking of covalent bond such that one electron goes to each of the atoms, forming free radicals

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2
Q

define heterolytic fission

A

breaking of covalent bond such that both electrons go to the SAME atom, forming +ve and -ve ions (cation being the carbocation)

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3
Q

what kind of bond cleavage forms free radicals?

A

homolytic fission

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4
Q

electrophiles are lewis acids or base?

A

acid

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5
Q

characteristics of electrophiles [3]

A
  1. are electron deficient
  2. attracted to regions of -ve charge or electron rich regions
  3. may possess an empty orbital to accept election pair
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6
Q

characteristics of radicals

A

contains unpaired electron formed from the homolytic fission of a covalent bond

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7
Q

does steric hindrance increase or decrease a moelcule’s reactivity? why?

A

decrease. prevents approach of an attacking reactant and either prevents reaction from taking place or lowers reactivity of a particular site within molecule

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8
Q

what is the electronic effect?

A

can be either electron withdrawing or donating.
An atom or a group of atoms can increase/decrease electron density to a compound. can understand it as the momentary giving/receiving of electrons

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9
Q

state the 2 broad groups of isomerism. differentiate the 2.

A

constitutional isomerism and stereoisomerism
constitutional: same molecular formula but diff structural formula
stereoisomerism: same molecular formula, same structural formula but diff spatial arrangement of functional groups

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10
Q

prefix name for -NO2

A

nitro-

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11
Q

prefix name for R-C=O [carbonyls]

A

oxo-

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12
Q

prefix name for -NH2

A

amino-

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13
Q

prefix name for -OH

A

hydroxy-

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14
Q

prefix name for -CN

A

cyano-

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15
Q

electrophilic addition occurs only in ___?

aka electrophiles added

A

alkenes

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16
Q

addition reactions occurs when compound is saturated or unsaturated?

A

unsaturated aka double bonds aka C=C or C=O bonds

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17
Q

nucleophilic addition occurs in what kinds of compounds? [2]

A

ketones and aldehydes

18
Q

define hydrolysis

A

a reaction which water is used to break a bond

19
Q

define condensation reaction

A

2 molecules react tgt to form a bigger molecule with elimination of small molecules eg. H2O, HCl

20
Q

oxidation occurs when ___ [4]

hint: what kinds of atoms are added/removed

A
  1. oxygen from oxidising agent is added
  2. H atom removed
  3. loss of electron
  4. increase in O.N
21
Q

state the 3 kinds of constitutional isomerism

A
  1. chain isomerism
  2. positional isomerism
  3. functional group isomerism
22
Q

what kind of constitutional isomerism do these compounds show?

A

chain isomerism
- essentially the same molecular formula C4H10 but differs in straight chain vs branched chain

23
Q

what kind of constitutional isomerism do these compounds show?

A

positional isomers
- functional groups located at different part of the same carbon skeleton

23
Q

what kind of constitutional isomerism do these compounds show?

A

positional isomers
- functional groups located at different part of the same carbon skeleton

24
Q

what is functional group isomerism? [2]

A

criteria to fulfill
1. both compounds have SAME molecular formula
2. but have different functional groups

25
Q

cis isomer has 2 identical groups on same/opposite side of the double bond?

A

same side

cis-same

26
Q

for cis-trans isomers, cis isomers has higher/lower boiling point than their respective trans-isomer? explain

A

higher. cis isomers have higher polarity so additional pd-pd forces require more heat energy to overcome

27
Q

criteria for enantiomerism [3]

A
  1. forms non-superimposable mirror image
  2. contains chiral centres
  3. does not have internal plane of symmetry
28
Q

a chiral carbon is ___-hybridised

type of hybridisation: sp/sp2/sp3 ?

A

sp3

29
Q

define racemic mixture

A

when theres is equal proportions of (+) and (-) enantiomers formed

30
Q

characteristics of meso compound [3]

A
  1. superimposable mirror image even though they contain chiral centres
  2. contains internal plane of symmetry [which causes point 1]
  3. optically inactive
31
Q

name the type of hybridisations & describe [3]

A
  1. sp hybridisation
    - 1 2s orbital combine with 1 2p orbital to form 2 identical sp orbitals
    - occurs when 2 σ bonds & 2 π bonds are formed
  2. sp2 hybridisation
    - 1 2s orbital combine with 2 2p orbital to form 3 identical sp2 orbitals
    - occurs when 3 σ bonds & 1 π bond is formed
  3. sp3 hybridisation
    - 1 2s orbital combine with 3 2p orbital to form 4 identical sp3 orbitals
    - occurs when 4 σ bonds are formed
32
Q

for IUPAC Naming, suffix is always the principal functional group. when there are more than 1 functional group, what is the order for precedence?

A

carboxylic acid / acyl halide / aldehyde / ketone > alcohol > amine > alkene

33
Q

characteristics of nucleophiles [3]

A
  1. are electron rich
  2. attracted to regions of +ve charge or electron deficient regions
  3. usually molecules with at least 1 lone pair of electrons
34
Q

criteria for cis-trans isomers [2]

A
  1. restricted rotation in certain parts of the molecule due to π bond
  2. 2 different groups attached to the same atom of the π bond
35
Q

why is the smallest cycloalkene to show cis-trans isomerism is cyclooctene?

A

the min no. of carbons in cycloalkanes to display cis-trans isomerism is 8. a cycloalkene with less than 8C gives only a cis isomer as the existence of a trans isomer will give rise to severe ring strain & hence instability.

36
Q

what’s the no. of possible cis-trans isomers present in a compound?

A

2^m , where m is the no. of double bonds that gives rise to cis-trans isomerism

37
Q

what’s the no. of enantiomers present in a compound?

A

2^n, where n is the no. of chiral centres

38
Q

what’s the no. of stereoisomers present in a compound which exhibits both cis-trans isomerism & enantiomers?

A

2^m+n, where m is the no. of double bonds exhibiting cis-trans isomerism & n is the no. of chiral centres exhibiting enantiomerism

39
Q

name all mechanisms for each functional group

A
  1. alkanes - free radical sub
  2. alkenes - electrophilic addition
  3. arenes - electrophilic substitution
  4. halogenoalkanes - nucleophilic sub
  5. carbonyls - nucleophilic addition

Organic Chemistry (9 decks)

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