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H2 Chemistry Organic Chemistry Factors

H2 Chemistry Organic Chemistry Factors

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Published by Yeo Zhi Ta Alan

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Published by: Yeo Zhi Ta Alan on Jun 30, 2011
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04/05/2013

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H2 Chemistry: Organic Chemistry!
Factors influencing:1.
 
Boiling and melting point:
-
 
Number of C atoms:
I
ncrease in number of C atoms >>increase in number of electrons>>Electron cloud of molecule more polarisable >> Stronger vander Waals forces >> Higher bp / mp-
 
B
ranched / straight-chain molecules:
 Straight-chain molecules >> Larger surface area >> Greater extensivenessof van der Waals interactions >> Higher bp / mp-
 
Cis / Trans isomers:
 
I
f substituents are polar, holding them in the cis-conformation will giverise to a net dipole moment, allowing them to form PD-PD interactions which are stronger than the
I
D-
I
D ones in trans-conformation>> Higher bpBut cis-isomers cannot pack as well into a crystalline structure as thetrans-isomer >> Less effective intermolecular forces >> Lower mp-
 
Sy 
mmetr
 y 
(meth
 y 
lbenzene vs. benzene onl
 y)
:
 Methylbenzene is less symmetrical >> Less efficient packing >> Weakerintermolecular forces >> Methylbenzene has lower mp
1
 -
 
P
resence (and number
)
of halogen atom(s
)
:
 Presence of halogen atom >>Larger number of electrons in HD molecule>>Electron cloud of molecule more polarisable >> Stronger van der Waals¶forces >> Higher bp / mp-
 
S
ize of halogen atom (if an
 y)
2
:
 
1
Methylbenzene has a higher bp though due to its higher number of C atoms 
2
Dominant factor (over changes in polarity of carbon ± halogen bond) in determining bp / mp inhalogen derivatives as effect of increases in ID-ID (due to increased number of electrons inhalogenoalkane molecule) outweighs the effect of decreases in PD-PD (due to decreased bondpolarity of C-halogen bond) from alkyl fluoride to alkyl iodide.
 
I
ncrease in size of halogen atom >>
I
ncrease in number of electrons (inmolecule) >> Electron cloud of molecule more polarisable >>Stronger vander Waals¶ forces >> Higher bp / mp-
 
P
resence of polar C=O group(carbon
 y 
l compounds, ac
 y 
l chlorides, esters
)
:
 Presence of polar C=O group >> Stronger PD-PD interactions (relative to
I
D-
I
D interactions) >> More energy required to overcome stronger PD-PDinteractions >> Higher bp / mp-
 
P
resence (and number
)
of ±OH groups
 
(alcohols, phenols, carbox
 y 
lic acids
)
:
 Presence of ±OH group >> Presence of hydrogen bonds
34
in addition to
I
D-
I
D interactions >> More energy required to overcome strongerhydrogen bonds in addition to
I
D-
I
D interactions >> Greater mp / bp-
 
D
imerisation(onl
 y 
in primar
 y 
and secondar
 y 
amides, andsometimes, carbox
 y 
lic acids
)
 Dimerisation>> Hydrogen bonds formed >> Higher bp / mp-
 
P
rimar
 y 
/
S
econdar
 y 
/ Tertiar
 y 
Amines (amines onl
 y)
:
 Primary and secondary amines >> Able to form strong hydrogen bonding between their molecules >> Higher bp / mp than tertiary ones (which canonly form weak van der Waals¶ forces)-
 
P
resence of zwitterions (onl
 y 
in amino acids
)
:
 Presence of zwitterions >> Strong electrostatic attraction betweenoppositely charged groups of zwitterions formed >> Higher bp / mp
2.
 
Solubility in water / polar solvents:
-
 
P
resence of non-polar h
 y 
drocarbon chains / benzene rings
 Presence of non-polar hydrocarbon chains / benzene rings>>Cannot formeffective polar interactions with water molecules for dissolving to occur >>
I
nsoluble
5
 
3
H
ydrogen bonds are stronger than PD-PD interactions (such as those in carbonyl compounds)
4
 
H
ydrogen bonds in carboxylic acids are stronger than those in alcohols as ±O
H
groups in ±COO
H
ismore polar due to presence of electron ± withdrawing carbonyl group.
5
Note:
Phenols
,
though having benzene rings
,
are still
slightly soluble
in
cold
water (emulsionformed) as hydrogen bonds can form between ±O
H
groups and water molecules (though slightlyhindered by benzene ring)
 
 -
 
L
ength of non-polar h
 y 
drocarbon chains
 Longer hydrocarbon chains >> Hinder formation of hydrogen bonds with water molecules >> Decreased solubility -
 
P
resence of polar ±OH, -COOH or C=O groups
6
 Presence of polar ±OH, -COOH or C=O groups >> Can form hydrogen bonds with water molecules >>
I
ncreased solubility ~-
 
P
resence of N atom (amines and amides onl
 y)
 Presence of N atom >> Presence of lone pair of electrons on N atom >> Ncan form hydrogen bonds with water molecules>> Soluble-
 
P
resence of zwitterions (amino acids onl
 y)
 Presence of zwitterions >> Can form ion-dipole interactions with watermolecules for dissolving to occur >> Soluble-
 
P
resence of polar R-groups (proteins onl
 y)
 Presence of polar R-groups >> Can form ion-dipole interactions orhydrogen bonds with water molecules for dissolving to occur >> SolubleNote: Even though HD molecules have the polar carbon-halogen bond,they are still insoluble as they cannot form hydrogen bonds with water
3.
 
 Acidity (Stability of anion of the dissociated acid)
I
ncreased stability of anion will lead to an increased acid strength-
 
P
resence of electron-withdrawing substituents
 Presence of electron-withdrawing substituents >> Delocalise the negativecharge about the anion >>
I
ncreased stability of anion >>
I
ncreased acidstrength-
 
P
resence of electron-donating substituents
 Presence of electron-donating substituents >>
I
ntensify the negativecharge about the anion >> Decreased stability of anion >> Decreased acidstrength-
 
Number of electron-donating / withdrawing substituents
 
I
ncreased number of electron-donating / withdrawing substituents >>Negative charge about the anion dispersed / intensified to a greater extent
6
E
xcept acyl chlorides since they hydrolyse rapidly in water.

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