ENGINEERING CHEMISTRY 3 (AAECH3A)
ASSIGMENENT 1: ALCOHOLS, ETHERS AND EPOXIDES
SUBMITION DATE: 17 APRIL 2023
TOTAL: 95 MARKS
Question 1
1. Give the IUPAC name of the following alcohols and state if the alcohol is 1⁰, 2⁰ or 3⁰
alcohol.
(a)
OH
CH3CHCH2CH2CH3
(4)
OH
H3CHC
(b)
(4)
OH
(c)
CH3
(4)
2. Predict the products of the following reactants:
(a)
CH3CH2CH2CH=CCH2CH3
CH3
(b)
1. BH3
2. NaOH, H2O2
(3)
1.Hg(OAc)2, H2O
2. NaBH4
(3)
(c)
CH2CH=CHCH2CH2CH2CH3
1. OsO4
2. NaHSO4, H2O
(3)
3. What reagent would you use to accomplish each of the following reactions?
(a)
OH
O
CH3CH2CH2CH
?
CH3CH2CH2CH2
(2)
O
(b)
CH3CH2CH2CH2CH2COH
4.
?
CH3CH2CH2CH2CH2CH2OH
(2)
What carbonyl compound would give the following alcohols on reduction with
LiAlH4
(a) CH3CH2CH2OH + CH3CH2OH
(3)
OH
CH2CCH3
(b)
(3)
5. Predict the product of the product of the following reactants.
O
(a) CH3CH2CH2CH2CH
1. CH3MgBr
2. H2O
(3)
O
1. CH3CH2MgBr
(b)
2. H2O
(3)
6. What is the starting carbonyl compound and Grignard reagent used to prepare the
following alcohols?
CH3
(a)
CH2=C-CH2OH
(5)
CH2OH
(b)
(5)
OH
(c)
CH3CHCH2CH3
(5)
7. What product are formed when reacting the following:
OH
(a) CH CH CH CH CH
3
2
2
2
2
OH
(b)
(c)
PCC
(2)
PCC
CH2CCH2CH3
CH3
(2)
OH
CrO3
CH3CH2CH2CHCH2CH2 H O+
3
(2)
Question 2
1.
(a)
(b)
(c)
2.
(a)
Draw the structure corresponding to the following IUPAC names.
Ethyl 1-ethylpropyl ether
Di(p-chlorophenyl) ether
Cyclopentyloxycyclohexane
(9)
Give the IUPAC name of the following ethers and epoxides.
CH3
CH3CH
(b)
O
OCH3
OCH3
(a)
O
CH3
(6)
3. Using Williamson Ether Synthesis, How will the following ethers be prepare?
(a) CH3CH2OCH2CH2CH3
Show all the steps
(6)
4. How will the following be prepared using Williams synthesis method?
(b)
CH3
CH-C-OH
CH3
?
CH3
CH3C
O
CH3
(4)
Predict the products of the following ether cleavage reactions
O-CH2CH3
HI
(a)
?
H2O
CH3
OCH2CHCH3
HBr
(a)
?
(6)
Predict the product of the following
O
(a)
H2O
?
-
OH
O
(b)
H2O
H+
?
(6)