Chemistry Reference
In-Depth Information
3.46
If the saturated hydrocarbon contained no rings, it would have the molecular formula
C
15
H
32
. Since there are fewer hydrogens in C
15
H
28
, it must have two rings (two
hydrogens are deleted per ring). Since caryophyllene absorbed 2 moles of H
2
(C
15
H
24
+ 2 H
2
→
C
15
H
28
), it must also have two double bonds or one triple bond. The
structure of caryophyllene follows:
CH
3
H
CH
3
CH
3
H
3.47
Water can donate a proton to a nucleophile:
-
-
H
O
H
+
Nu
Nu
H+
H
O
or an oxygen lone pair to an electrophile:
+
E
+
H
O
H
+
H
O
H
E
3.48
CH
3
CH
3
OH
CH
3
2
O, H
+
H
+
CH
3
CH
2
CH
3
CH
2
CH
3
CH
2
OH
In each case, water adds according to Markovnikov's rule (via a tertiary carbocation).
The diol is:
CH
3
OH
CH
3
CH
3
OH
3.49
The ion has a symmetric structure.
+
+
(C H)
2
CHCH
CH
CHCH(C
H)
2
(C H)
2
CHCH
CH
CHCH(C
H)
2
