Nomenclature

Sunday, October 16, 2022 9:06 PM

Naming substituted thiols: Common names

1. Longest carbon chain
containing the - SH group
2. Name carbon chain based
on preference to the -SH
3. Presence of functional
group higher priority than Propyl thiol/propyl mercaptan
thiol: -mercapto/mercaptan
(treat as functional group, not
parent name)
4. Alcohol is higher prio than
thiol
Isopropyl
thiol/isopropyl
mercaptan

Cyclohexyl
thiol/cyclohexyl
marcaptan

1. 4-methyl-2-pentanethiol

3-mercapto-1-propanol
3-sulfanyl-1-propanol

3-bromo-2-chlorocyclobutanethiol 3-mercapto-2-octanol

(1S,4R)-4-methoxy-2,2-
dimethylcyclohexanethiol
2-chloro-1-cyclopentanethiol
l
 dimethylcyclohexanethiol
2-chloro-1-cyclopentanethiol

3-butene-1-thiol
(butene starts at 3)

3-methyl-3-hexanethiol

3-sulfanyl-1-propanol
(alcohol has higher prior

1,4-butanedithiol

Methylcyclobutanethiol

Boiling point:
1. Higher number of o atoms
2. Higher number of carbon atoms
3. Lower branching carbon atoms
3-bromo-3-chloro-2-butanethiol
Ether- ch3-o-ch3/r-o-r:
If hydrogen bonding is existing, higher boilin
point. Ether has no hydrogen bonding becau
r-o-r, hence oxygen is not directly bonded t
hydrogen.

Solubility:
1. More electronegative elements
2. Net dipole moment: big deviation car
c - 2.1 and hydrogen is 3
3. Lower carbon atoms:
4. More branched: give more electron d
 l

rity)

ng
use of
to

rbon is

density