CHM 201

Roadmap Problems

1. An unknown compound (A) has a formula of C7H8. Treatment of A with H2 on

Lindlar's catalyst gives compound B (C7H12). Treatment of A with H2/Pd on carbon
(standard hydrogenation) gives compound C (C7H16). Ozonolysis of B followed by a
Zn/acetic work-up gives pentanedial and 2 equivalents of formaldehyde.
H2 on Lindlar's cat.
A (C7H8) B (C7H12)
H2, Pd on C
C (C7H16)

O O O
1) O3
2 eq. HCH + HCCH2CH2CH2CH
2) Zn, HOAc

Propose structures for A, B, and C that are consistent with these data.
Compound A has 4 degrees unsaturation
reaction with H2, Lindlar's catalyst results in the reaction
w/ 2 mol equivalents of H2 , thus 2 triple bonds reacted

H2
Lindlar's cat.
A B
H2
Pd/C
C

1) O3 O O
2) Zn, HOAc
B + 2 HCHO

2. An unknown compound (A) has a formula of C8H12. Treatment of A with H2/Pd-

carbon gives B (C8H16). Treatment of A with H2 on a Lindlar catalyst gives no reaction.
Ozonolysis of A followed by workup with Zn, HOAc affords 2,4-pentanedione and
propanedial shown below.
H2 / Pd on carbon
A B
C8H12 C8H16

H2 / Lindlar's cat. no rxn

O O
1) O3 +
2) Zn, HOAc H H
O O
 There are 3 sites of unsaturation in A.

a) How many double bonds does A have? 2 (2 eq. of H2 reacted)

b) How many triple bonds does A have? 0 (no rxn w/ H2, Lindlar)

c) How many rings does A have? 1 (one site remains)

d) Propose structures for both A and B that are consistent with these data.

A B