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ORGLAB QUIZ REVIEWER

Solubility
- The ability for a given substance, the solute, to dissolve in a solvent
- Solute: the substance that is dissolved in a solution
- Solvent: a liquid used for dissolving other substances, present in greater amounts than the
solute
- Factors:
Ratio of solute to solvent
Temperature
Intermolecular forces
- Strong solvent-solute dissolution is favored
Molecular size
- A thing to remember: compounds with 4 or less carbons are soluble in H2O as long
as they contain O, N, or S

ALKANE RING
- Neutral

Sample H2O 1M HCl (acid) 1M NaOH (base)

Cyclohexane Immiscible Immiscible Immiscible


cyclohexane is non- No reaction No reaction
polar while H2O is polar
Unreactive
saturated

AMINE
- Basic
Turns limitus paper blue
Has a lone pair of electrons to give
Easily dissolves in acids such as HCl
- In terms of basicity, 2 > 1
More inductive effect, more negative more ready to get protons/H+
BUT 3 is the least stable!!!!

Sample H2O 1M HCl (acid) 1M NaOH (base)

Ethylamine Miscible Miscible Miscible


2C = 1 Reaction occurs No reaction

Triethylamine Immiscible Miscible Miscible


6C = 3 more carbons = more Reaction occurs No reaction
non-polar = harder to
dissolve in H2O

1, 6-hexanediamine Miscible Miscible Miscible


6C = 1 has two 1 amine Reaction occurs No reaction
groups which can form
more H-bonds with H2O
[ insert acid-base reaction here later]
ESTER
- Neutral
- Slow reaction with H2O = hydrolysis

Sample H2O 1M HCl (acid) 1M NaOH (base)

Isoamyl acetate Immiscible Miscible Miscible


- 7C No OH group, cannot Reaction occurs Reaction occurs
form H-bond CA + OH via acid- CA + OH via base-
Lots of carbon = non- catalyzed reaction w catalyzed reaction w
polar lots of odor lots of odor
[ insert acid-base reaction here later]

ALCOHOL
- Weak base and weak acid neutral
- Can only react with metal hydroxides to a limited extent
- Can react with metal hydrides (ex. NaH) and NaNH2 (strong base)

Sample H2O 1M HCl (acid) 1M NaOH (base) 1M NaHCO (acid/


base)

Ethanol Miscible Miscible Miscible Miscible


2C = 1 - OH is capable of Reaction occurs No reaction No
forming H-bonds effervescence
with

N-pentanol Immiscible Miscible Miscible Immiscible


5C = 1 more carbons = Reaction occurs No reaction No
N- = straight more non-polar effervescence
chain

ALCOHOL + AROMATIC RING


- Weak acid

Sample H2O 1M HCl (acid) 1M NaOH (base) 1M NaHCO (acid/


base)

Phenol Immiscible Immiscible Miscible Immiscible


6 carbons = too No reaction Reaction occurs No reaction
non-polar to be acid-base weak acid +
dissolved in water reaction weak base does
not form a reaction
[ insert acid-base reaction here later]

CARBOXYLIC ACID + AROMATIC RING


- Relatively weak acid but stronger than phenol
Sample H2O 1M HCl (acid) 1M NaOH (base) 1M NaHCO (acid/
base)

Benzoic acid Insoluble Insoluble Soluble Soluble


(solid) 6 carbons = too No reaction Reaction occurs Reaction occurs
non-polar to be acid-base with
dissolved in water reaction effervescence
strong enough
acid to react with a
weak base
[ insert acid-base reaction here later]