Name: ________________________________

Organic Reactions Worksheet

For the questions below, give full structural diagrams and names for all reactants and products. Also indicate
any catalysts/reaction conditions for the reaction. Also indicate the TYPE OF REACTION.
1. The reaction between benzene and 2 moles of chlorine gas.
Cl

AlCl3
+ 2 Cl Cl
+ 2 H Cl
Cl
benzene meta-dichlorobenzene

Substitution Reaction
2. The formation of 2-hexanol from an alkene.
H2SO 4 OH
+ H2O
100 C
1-hexene 2-hexanol

Addition Reaction
3. The formation of 2,2-pentanediol.
OH
H2SO4
+ 2 H2O
100 C OH
1-pentyne
2,2-pentanediol

Addition Reaction
4. The reaction between 3-hexanol and potassium dichromate. What would you visually observe during the
reaction?
K 2 Cr 2 O 7
+ H2O

OH O
3-hexanol 3-hexanone
dichromate changes from orange to green

Oxidation Reaction
5. The reduction of butanal.
Pt
O + H2
101 MPa
OH
butanal 1-butanol

Reduction Reaction (Addition Reaction)

6. The formation of the most common dinitrobenzene.
H2SO4 NO2
+ 2 HNO3 + 2 H 2O

NO2
Substitution Reaction
7. The formation of dimethyl amine from ammonia.
 Name: ________________________________
NH3 + 2 Cl CH3 H3C NH + 2 HCl
ammonia chloromethane CH3 hydrogen chloride
N-methylaminomethane

Substitution Reaction

8. The reaction between trans-2-hexene with hydrogen bromide.

Br

+ HBr +
2-bromohexane
trans-2-hexene hydrogen bromide Br
3-bromohexane

Addition Reaction

9. The formation of ethyl benzoate.

O O
H 2S O 4
O
OH + OH + H 2O
heat
ethanol ethyl benzoate
benzoic acid

Condensation Reaction

10. The reaction that would occur if isopropanol was heated at 140°C in acidic conditions.
HO H 2S O 4
O + H2O
1 4 0 �C
isopropanol isopropoxy-2-propane

Condensation Reaction

11. The reaction that would occur if isopropanol was heated at 100°C in acidic conditions.
HO H 2S O 4
+ H2O
1 0 0 �C
isopropanol propene

Elimination Reaction

12. The formation of 2-butanol.

H 2S O 4
OH
+ H2O
1 0 0 �C
1-butene 2-butanol

Addition Reaction
-could also use 2-butene

13. The formation of phenyl benzoate.

O OH O
H 2S O 4
O
OH + + H2O
heat

benzoic acid hydroxybenzene

phenyl benzoate
Condensation Reaction
14. The reaction that would occur if ethyl propanoate was heated in the presence of water and acid.
 Name: ________________________________
O O
H 2S O
O + H2O 4
OH + HO
heat ethanol
ethyl propanoate propanoic acid
15. The hydrolysis of N-methyl ethanoate.
O O
H 2S O 4
+ H2O
OH + H2N CH3
heat
NH propanoic acid aminomethane
N-methylpropanamide
Hydrolysis
16. The reaction between 2 moles of water with 2-pentyne.
OH OH
H2SO4
+ 2 H2O
100 C
+
OH OH
1-pentyne
2,2-pentanediol 3,3-pentanediol

Addition Reaction
17. The oxidation of 2-butanol. Describe the qualitative observations for this reaction.
OH KM nO 4
O
+ H2O

2-butanol butanone

- KMnO4 changes from purple to brown

- K2Cr2O7 will change from orange to green

Oxidation Reaction
18. The oxidation of 1-butanol. Show any intermediates formed and describe the qualitative observations.
KM nO O KM nO O
OH 4
+ H2O
4
+ 2 H+
HO
1-butanol butanal butanoic acid

- KMnO4 changes from purple to brown (K2Cr2O7 will change from orange to green)

Oxidation Reaction
19. The complete and incomplete combustion of 2-pentanol.
OH
+ 15/2 O O 5O C O + 6 H2O
2-pentanol
Complete Combustion
OH
+ 6O O 3O C O + C + C O + 6 H2O

2-pentanol
Incomplete Combustion
 Name: ________________________________
20. The reaction between t-butyl alcohol and hydrogen chloride. Describe any qualitative observations.
Z n C l2
OH + HCl Cl + H2O

methyl-2-propanol 2-chloro-2-methylpropane
Substitution Reaction
- would form a precipitate immediately

21. You have an alcohol with the formula C4H10O. Describe a qualitative test that you could conduct to
determine the structural formula of the alcohol. Show a full reaction including the qualitative
observations for each of the possibilities.

It could be 1-butanol, 2-butanol or t-butyl alcohol. To determine which alcohol it was you would conduct the
Lucas test. Mix the compound with hydrogen chloride in the presence of zinc chloride. The primary alcohol
(1-butanol) would take much longer than 5 min to precipitate, the secondary alcohol (2-butanol) would take
about 5 min to form a precipitate and the tertiary alcohol (t-butyl alcohol) will form a precipitate immediately.
Z n C l2
+ Cl
HO HCl + H2O
1-chlorobutane
1-propanol

Z n C l2 Cl
OH
+ HCl + H2O

2-propanol 2-chlorobutane

Z n C l2
OH + HCl Cl + H2O

2-methylpropan-2-ol 2-chloro-2-methylpropane
22. Describe a qualitative test that you could conduct to distinguish between propanal and propanone. Show
a full reaction including the qualitative observations for both compounds.
Oxidation Reaction

O a n y o x id iz in g a g e n t O
p ic k 1 HO
+ 2 H+
propanal propanoic acid

O a n y o x id iz in g a g e n t
NO REACTION
p ic k 1
propanone
KMnO4 turns from purple to brown in propanal
K2Cr2O7 turns from orange to green in propanal
Fehling's (copper 2 solution) turns from blue to a copper ppt in propanal
Tollen's turns from colourless to a black ppt and silver mirror in propanal
 Name: ________________________________
23. Show the formation of 2-butene from an alcohol.
OH H SO2 4 + H2O
1 0 0 �C
2-butanol 2-butene

Elimination Reaction
- also produce 1-butene

24. Show the reaction between methanol and butanoic acid.

OH H SO 2 4 + H2O
1 0 0 �C
2-butanol 2-butene

Elimination Reaction
- also produce 1-butene

25. Show the reaction between water and cyclohexene.

OH
H 2S O 4

+ H2O
1 0 0 �C

Addition Reaction