12 U Organic Chemistry Worksheet # 4 – Organic Functional Group Reactions
1. Write the balanced chemical reaction for the following combustion reactions. Assume complete combustion.
a) ethanol + oxygen
d) hexan-2,3-diol + oxygen
b) 2-methylbutan-1-ol + oxygen
e) cyclopropanol + oxygen
c) 2,4-dimethylpentan-3-ol + oxygen
f) phenol + oxygen
2. Complete the following elimination reactions involving alcohols.
CH3
OH
CH
CH
CH3
H2C
HO
CH2
CH3
a)
CH2
→
b)
CH3
CH
CH
CH3
CH3
→
CH2
H2C
CH2
c) HO
CH2
CH2
OH
CH2
→
CH2
d)
OH
CH
CH2
→
3. How could you make pentane from pentan-2-ol? Devise a pathway using a two-step reaction. (*Hint –
elimination is the first step!)
4. Why are substitution reactions involving alcohols slow?
5. Complete the following substitution reactions involving alcohols.
OH
CH2
HC
HO
CH3
a) H3C
HO
+ HBr →
CH2
CH2
b)
CH2
CH3
CH2
CH2
+ HI →
CH3
CH
HC
CH3
CH2 C
c) H3C
d) H3C
OH + HCl →
OH
CH2
CH3
+ HF →
6. Complete the following substitution reactions involving amines.
H
N
H
CH2
+ H3C
a) H
Cl
CH2
CH2
→
b) H3C
CH2
NH
CH2
H3C
CH2
c)
H3C
CH2
CH2
NH
CH3
CH3
+F
CH2
CH3
CH
NH2
CH2
→
CH2
+ H3C
Br →
d)
7. What does the term “oxidation” mean for organic reactions?
8. What does “controlled oxidation” mean compared to just “oxidation?”
CH3
+
H3C
Cl
9. Why do some oxidations of alcohols create an aldehyde, and others a ketone?
10. Complete the following oxidation reactions involving alcohols.
H3C
CH2
a) H3C
CH2
CH2
OH + [O] →
CH
CH2
OH
b)
CH3
HC
CH3
CH2
CH3
CH
c) HO
H2C
CH3
OH + [O] →
OH
CH
H2C
CH
CH2
+ [O] →
CH2
CH2
d)
+ [O] →
11. How could you make butanone from an alkene? Devise a pathway using a two-step reaction. (*Hint – oxidation
is the second step!)
12. Complete the following oxidation reactions involving aldehydes.
H3C
CH3
CH HC
O
HC
CH
CH2 CH3 + [O] →
a)
b)
CH3
+ [O] →
O
O
H3C
CH2
CH
CH2 HC
CH
+ [O] →
Br
c)
+ [O] →
d) O
13. How could you make a carboxylic acid starting from 1-propanol? Devise a pathway using a two-step reaction.
(*Hint – oxidation is the second step!)
14. When a bottle of wine is left open to the air for a period of time, the wine often loses its alcoholic content and
starts to taste sour. Write a series of equations to illustrate the reactions.
15. Complete the following reduction reactions involving aldehydes and ketones.
O
C
H2C
CH3
CH2
CH2
a)
CH3
+ [H] →
b) H3C
CH2
CH2
CH
CH2
O
CH2
CH2
HO
O
HC
C
CH2
c)
CH2
+ [H] →
d) H3C
CH2
CH2
O
CH
+ [H] →
+ [H] →
16. How could you make bromoethane from ethanal? Devise a pathway using a two-step reaction. (*Hint –
reduction is the first step!)
17. Complete the following reduction reactions involving carboxylic acids.
O
CH2
H3C
CH2
CH2
HO
O
C
+ [H] →
Br
H3C
b)
CH3 + [H] →
O
CH
CH2
CH
CH2
C
CH2
O
OH
C
CH3
c)
CH3
CH HC
OH
a)
H3C
C
+ [H] →
CH3
+ [H] →
d) HO
18. How could you make pentan-1-ol from pentanoic acid? Devise a pathway using a two-step reaction. (*Hint –
reduction is the first step!)
19. Complete the following condensation reactions between two alcohols.
H3C
CH
OH
CH2
a) H3C
CH2
H3C
CH
OH + H3C
CH2
CH3 →
CH2
HC
CH3
+ H3C
OH
b)
OH
→
OH
CH
CH3
CH2
c)
H3C
H2C
HO
CH
CH2
OH
CH2
CH2
+
CH2
CH2
CH3
CH2
HO
→ d)
CH3
CH2
CH3
CH2
+
CH3
→
20. In condensation reactions, water is removed. When a carboxylic acid and an alcohol are involved, which one
loses an OH and which an H atom?
21. Complete the following condensation reactions between carboxylic acids and alcohols.
O
CH2
a) H3C
CH2
CH2
OH
CH2
C
+
HO
CH2
CH2
O
OH
CH2
b) H3C
C
CH2
CH
OH + H3C
CH3 →
CH3
CH2
→
O
C
CH2
c) H3C
HO
OH
CH2
CH3
CH2
CH2
C
CH3
CH2
H3C
+
→
H3C
CH2
H2C
CH2
O
CH
CH2
CH3
CH2
CH2
C
d) H3C
OH +
→
OH
22. Devise a pathway to create an ester with the starting materials of propanal and but-2-ene. (*Hint – each
reactant needs to be converted to something else before the esterification can occur).
23. In condensation reactions, water is removed. When a carboxylic acid and an amine are involved, which one
loses an OH and which an H atom?
24. Complete the following condensation reactions between carboxylic acids and amines.
O
CH2
C
CH2
CH2
CH3
CH2
CH2
+ H3C
OH
a)
CH2
CH2
NH2
CH2
→
O
CH2
b) H2N
+ H3C
CH2
H3C
CH2
CH3
CH2
CH
CH2
CH2
CH2
CH3
O
OH
+ H3C
NH2
d)
CH2
→
CH3
CH
+ HO
CH3
NH
CH3
C
CH3
CH2
CH2
O
CH
H3C
OH →
C
CH2
c)
C
CH3
CH
CH2
CH
CH2
CH3 →
25. Devise a pathway to create an amide with the starting materials of butanone and propane. (*Hint – each
reactant needs to be converted to something else before the esterification can occur).
26. Complete the following hydrolysis of esters reactions.
O
CH2
a) H3C
CH2
CH2
O
C
O
CH2
CH2
CH3
CH2
C
+ H2O →
b) H3C
CH2
O
CH3
CH2
+ H2O →
H3C
CH2
CH3
H3C
c)
O
CH
CH
O
CH
C
CH3
O
CH2
CH2
CH2
Cl
CH3
+ H2O →
O
CH
CH
CH2
+ H2O→
Cl
d)
27. How can you make propanol and pentan-3-ol from an ester? Devise a pathway using a two-step reaction.
(*Hint – hydrolysis is the first step!)
28. Complete the following hydrolysis of amides reactions.
O
H3C
C
CH2
CH
N
CH3
O
CH3
CH2
a) H3C
C
NH
H2C
CH2
CH2
CH2
CH3
+ H2O →
CH3
b)
+ H2O →
O
CH2
H3C
CH2
CH2
C
CH2
CH3
CH2
c)
O
OH
C
CH
N
CH3
+ H2O →
d) H3C
NH
CH2
CH3
+ H2O →