Alkanes Flashcards

1
Q

What has the general formula CnH2n?

A

Cycloalkanes - with only 1 ring

Alkenes

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2
Q

Phy. properties of alkanes (4)

A
  1. IMF - essentially np - relatively weak instantaneous dipole-induced dipole interactions
  2. BP & MP
    - Increases with increasing no. of C - as the no. of C atoms in alkanes increases, the no. of e- per alkane molecule increases and the size of e- cloud increases. Hence, the ease of polarising the e- cloud increases, leading to increasing strength of instantaneous dipole-induced dipole attractive forces which are overcome at increasingly higher temp
    - Decreases with increasing degree of branching
    With branching, the molecule becomes more spherical and its surface area available for intermolecular interactions decreases. This reduces the extent of contact b/w neighbouring molecules, resulting in weaker instantaneous dipole-induced dipole forces that are overcome at a lower temp
  3. solubility
    Being essentially np, alkanes are soluble in np solvents such as benzene and insoluble in water and other highly polar solvents
    Some l alkanes are used as np solvents - dissolve compounds of low polarity and do not dissolve compounds of high polarity
  4. Density
    Density increases with increasing molecular size of the alkanes but tend to lvl off at abt 0.8 gcm^-3
    ALL LESS DENSE THAN WATER
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3
Q

Carbon & Hydrogen atoms being classified as primary (1°), secondary (2°), tertiary (3°) or quaternary (4°) - how it looks like

A

A 1°C atom is bonded to 1 other C atom …….
A 1°H atom is bonded to a C atom that is bonded to 1 other C atom
A 2°H atom is bonded to a C atom that is bonded to 2 other C atom

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4
Q

which alkanes are gas, liquid, gas?

A

Gas: methane, ethane, propane, butane
Liquid: Pentane, hexane, heptane, octane, nonane, decane, undercane…
Gas: … Icosane… ??

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5
Q

Reduction of alkenes (2)

A

Reduction of Alkenes -> alkanes

Reagent & Conditions: H2(g) & Ni & heat OR H2(g) & Pt/Pd

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6
Q

Reduction of other unsaturated hydrocarbons: Alkynes & benzene

A

Alkynes can be reduced to alkanes under suitable conditions
CH3C三CH (Propyne) + 2H2 —-(Pd)—–> CH3CH2CH3 (Propane)

Benzene can also be reduced to cyclohexane under suitable conditions
Benzene + 3H2 —-(Ni Catalyst, high temp, high pressure)—> cyclohexane

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7
Q
Reactions of alkanes with polar reagents:
NaOH (aq)
HCL (aq)
Conc H2SO4 
Acidified KMnO2 (aq) 
Air (O2) 
Bromine
A

NaOH (aq), HCL (aq), Conc H2SO4: No effect, 2 immiscible layers observed
Acidified KMnO2 (aq): No decolourisation of purple KMnO4 even on heating, 2 immiscible laters observed
Air (O2): No effect when cold. Burns when heated
Bromine: No effect in the dark. bromine decolourised in the presence of sunlight

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8
Q

The general reactivity of alkanes can be attributed to the following reasons: (2)

A
  1. NP
    - they do not contain any region of high e- density (no C=C/C三C) & thus do not attract electrophilic reagents
    - do not contain any e- deficient sites (no C=O bonds) to attract nucleophilic reagents
  2. Alkanes have relatively strong C-C & C-H bonds which do not break under normal conditions
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9
Q

Reactions of Alkanes with np reagents (under right conditions)
(2)

A

Combustion & Halogenation (mechanism: free radical substitution)

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10
Q

Combustion of alkanes - exo? - complete n incomplete - general eqn for complete?

A

Burns readily in air or oxygen when ignited - very exo, impt source of fuel

Complete combustion produces CO2(g) & H2O (l) - non sooty flame
Combustion of a hydrocarbon: CxHy + (x+y/4) O2(g) -> xCO2(g) + y/2 H2O

Incomplete combustion leads to formation of CO (g) & C (as soot) in addition to CO2(g) & H2O(l) - sooty flame

CH4(g) + 3/2O2(G) -> CO (g) + 2H2O (l)
CH4(g) + O2(g) -> C(s) + 2H2O (l)

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11
Q

Defn of Free radical & characteristics eg electrically…

A

Free radical is an atom or grp of atoms that has an unpaired e-

  • highly reactive & are intermediates in many rctns of alkanes
  • electrically neutral as same no. of protons n e-
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12
Q

Stability of alkyl radicals & reason

A
Depends on the no. of alkyl grps ('R') attached 
Methyl radical (0 R) < primary alkyl radical (1 R) < secondary alkyl radical (2 R) < tertiary alkyl radical (3 R) - most stable

Reason: The carbon with the unpaired e- is e- deficient. As alkyl groups are e- donating, the more alkyl grps attached to the carbon with the unpaired e-, the more stable the alkyl radical

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13
Q

Defn of homolytic fission of a covalent bond

A

occurs when the bond breaks in such a way that each of the atoms involved in forming the bond acquires one of the 2 bonding e-, thus forming free radials

(EQUAL SHARING OF E-)

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14
Q

Halogenation of an alkane involves … (defn)
Reagents:
Condition:
Mechanism:

Conducted in what state?

A

Halogenation of an alkane involves the substitution of 1 or more hydrogen atoms of the alkane by halogen atoms
Reagents: Cl2 or Br2
Condition: UV light or Heat
Mechanism: Free radical substitution

Conducted in liquid or gaseous state, not aq as water molecules will react with any radical present.

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15
Q

HCl in frs is called ___ not ____

A

Hydrogen chloride not hydrochloric acid cuz cant be aq state

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16
Q

Describing Free-radical substitution steps (8)

A

Name mechanism: Free radical substitution

Heading for 3 steps: Step 1: initiation, Step 2: propagation, Step 3: termination (basically combine all radicals)

Conditions for initiation: UV light/heat

Half arrows from the bond to halogen atoms in initiation step

Label propagation steps (a) & (b),

Then (a), (b), (a), (b)…

The termination steps must include a rctn which forms the required product (AT LEAST 3 products)

Placing of . on correct atoms in all steps

17
Q

What to write when using additional propagation steps to generate prod

A

Propagation steps (a) & (b) give rise to many molecules of CH3CHBrCH3, which can undergo further bromination via propagation steps (c) & (d) to form CH3CHBrCH2Br

(c) the prod of (b) -> ……
(d) ….

Termination: all the radicals from (a) to (d)

18
Q

Finding proportion of prod in f.r.s.

& factors affecting ^ (2)

A
  1. Ratio of diff types of H atoms in an alkane
  2. Stability of carbon radical intermediate

Ans: Based on probability factor and assuming all H atoms have the same reactivity, the approx molar ratio of G to H = 2:12 (secondary H atom: pri H atom)

OR
For qn with relative rate:
Ans: Combining both the probability factor & the reactivity ratio factor ( given: 1 n 21) ,
the relative ration of A to B = (1)(21) : (9)(1) = 7:3

19
Q

When propane is chlorinated, the ratio of the 2 prod formed in a 1:1 ratio instead. Suggest an explanation for the diff b/w this ratio and the expected ratio from (a)

A

The expected ratio is obtained by assuming that all H atoms have the same reactivity. (A) is formed from .CH2CH2CH3 intermediate while (B) is formed from CH3.CHCH3, which is a 2° radical that is more stable than .CH2CH2CH3, a 1° radical. Due to the presence of 1 more e- - donating alkyl grp attached to the e- deficient C atom, there’s a greater proportion of (B) than expected.