CHM 2211C Exam II Summer 2024 — 100 points Name: KEN
Measurable Course Objectives Addressed in this Exam
e Write products and complete stepwise mechanisms for the reactions and synthesis of ethers
e Write products and complete stepwise mechanisms for the reactions and synthesis of aldehydes and ketones
» Provide a logical and realistic set of reactions that will convert a given starting material to a desired end product
The total point value for this exam exceeds 100 points. The extra points are extra credit. It is possible to achieve an exam
grade of over 100 points or greater than 100%. \30
Directions: For the following multiple choice questions, choose the most correct answer.
1) (1.5 pts) An ether is more volatile than an alcohol having the same molecular formula. What is the reason for this
difference?
a. Alcohols have resonance structures.
b. Dipole nature of ethers.
¢. Intermolecular-hydrogen bonding in ethers.
@ Intermolecular-hydrogen bonding in alcohols.
2) (1.5 pts) Ethers may be used as solvents because they react only with which of the following reactants?
(a) Acids
b. Bases
c. Oxidizing agents
d. Reducing agents
3) (1.5 pts) What are the products when ethyl isopropyl ether is cleaved with concentrated HI?
|°
a. Ethanol and 2-iodo-2-methylpropane 20 H Su2
~
b. Ethanol and 2-methylpropane o /k X
@) Todoethane and isopropyl alcohol o~
d. Iodoethane and 2-methylpropane e ne (
4) (1.5 pts) Which pair of products would result from the acid cleavage of tert-butyl propyl ether with excess
concentrated HBr at an elevated temperature?
a. 2-methyl-2-buten¢ and propyl bromide +°_')zo R SN\
b Tert-butyl alcohol and propyl bromide
Tert-butyl bromide and propy! alcohol —-o- | ——/l
@) Tert-butyl bromide and propyl bromide B
5) (1.5 pts) What are the products when tert-butyl ethyl ether is cleaved with concentrated HI?
a. lIodoethane and tert-butanol 3° o
b. Todoethane and 2-iodo-2-methylpropane _\__ o—" WT
(¢, Ethanol and 2-iodo-2-methylpropane.
d. Ethanol and tert-butanol
41 wo —
, 6) (1.5 pts) What is the major product formed when ethanol is dehydrated with concentrated H,SO;4 at 413K?
a. Ethene
Ethoxy ethane
¢. Methoxy ethane
d. Methoxy ethane T, _,
7) (1.5 pts) Which pair of products would result from the acid cleavage of phenyl propy! ether with excess
concentrated HBr at an elevated temperature?
SP-' co*ion rot lvab\e
a. Bromobenzene and 1-propanol @‘ S ‘)
b. Bromobenzene and 1-bromopropane - J
(¢) Phenol and 1-bromopropane @ & S
d. Phenol and 1-propanol
8) (1.5 pts) The reaction between tert-buty! chloride and sodium ethoxide gives .
a. butene
(b) 2-methylprop-1-ene —-\— c No'-"OE+ ER vxn
c. tert-butyl ethyl ether
d. tert-butyl methyl ether —F
9) (1.5 pts) Select the ether among the following that yields methanol as one of the products on reaction with cold
hydroiodic acid.
ME& e ome
y
a. 1-methanoxybutane
1-methoxy-2-methylpropane
P 4
(©) 2-methoxy-2-methylpropane
d. methoxybenzene
10) (1.5 pts) The boiling point of ethanol is much higher than that of dimethyl ether though both have the same
molecular weight. Why?
a. The dipole moment of ethanol is less.
b. Dimethyl ether is insoluble in water
@ Ethanol exhibits hydrogen bonding
d. Methyl groups are attached to oxygen in ether.
11) (1.5 pts) Which of the following is not favorable for the proper dehydration of alcohol to form ether?
a. Excess alcohol.
b. Good temperature control during reaction.
) Presence of bulky alkyl groups in the alcohol.
d. Presence of protic acids.
12) (1.5 pts) Which of the following is the least reactive functional group?
a. Alcohols
b. Aldehydes
@ Ethers
d. Ketones
Measurable Course Objectives Addressed in this Exam
e Write products and complete stepwise mechanisms for the reactions and synthesis of ethers
e Write products and complete stepwise mechanisms for the reactions and synthesis of aldehydes and ketones
» Provide a logical and realistic set of reactions that will convert a given starting material to a desired end product
The total point value for this exam exceeds 100 points. The extra points are extra credit. It is possible to achieve an exam
grade of over 100 points or greater than 100%. \30
Directions: For the following multiple choice questions, choose the most correct answer.
1) (1.5 pts) An ether is more volatile than an alcohol having the same molecular formula. What is the reason for this
difference?
a. Alcohols have resonance structures.
b. Dipole nature of ethers.
¢. Intermolecular-hydrogen bonding in ethers.
@ Intermolecular-hydrogen bonding in alcohols.
2) (1.5 pts) Ethers may be used as solvents because they react only with which of the following reactants?
(a) Acids
b. Bases
c. Oxidizing agents
d. Reducing agents
3) (1.5 pts) What are the products when ethyl isopropyl ether is cleaved with concentrated HI?
|°
a. Ethanol and 2-iodo-2-methylpropane 20 H Su2
~
b. Ethanol and 2-methylpropane o /k X
@) Todoethane and isopropyl alcohol o~
d. Iodoethane and 2-methylpropane e ne (
4) (1.5 pts) Which pair of products would result from the acid cleavage of tert-butyl propyl ether with excess
concentrated HBr at an elevated temperature?
a. 2-methyl-2-buten¢ and propyl bromide +°_')zo R SN\
b Tert-butyl alcohol and propyl bromide
Tert-butyl bromide and propy! alcohol —-o- | ——/l
@) Tert-butyl bromide and propyl bromide B
5) (1.5 pts) What are the products when tert-butyl ethyl ether is cleaved with concentrated HI?
a. lIodoethane and tert-butanol 3° o
b. Todoethane and 2-iodo-2-methylpropane _\__ o—" WT
(¢, Ethanol and 2-iodo-2-methylpropane.
d. Ethanol and tert-butanol
41 wo —
, 6) (1.5 pts) What is the major product formed when ethanol is dehydrated with concentrated H,SO;4 at 413K?
a. Ethene
Ethoxy ethane
¢. Methoxy ethane
d. Methoxy ethane T, _,
7) (1.5 pts) Which pair of products would result from the acid cleavage of phenyl propy! ether with excess
concentrated HBr at an elevated temperature?
SP-' co*ion rot lvab\e
a. Bromobenzene and 1-propanol @‘ S ‘)
b. Bromobenzene and 1-bromopropane - J
(¢) Phenol and 1-bromopropane @ & S
d. Phenol and 1-propanol
8) (1.5 pts) The reaction between tert-buty! chloride and sodium ethoxide gives .
a. butene
(b) 2-methylprop-1-ene —-\— c No'-"OE+ ER vxn
c. tert-butyl ethyl ether
d. tert-butyl methyl ether —F
9) (1.5 pts) Select the ether among the following that yields methanol as one of the products on reaction with cold
hydroiodic acid.
ME& e ome
y
a. 1-methanoxybutane
1-methoxy-2-methylpropane
P 4
(©) 2-methoxy-2-methylpropane
d. methoxybenzene
10) (1.5 pts) The boiling point of ethanol is much higher than that of dimethyl ether though both have the same
molecular weight. Why?
a. The dipole moment of ethanol is less.
b. Dimethyl ether is insoluble in water
@ Ethanol exhibits hydrogen bonding
d. Methyl groups are attached to oxygen in ether.
11) (1.5 pts) Which of the following is not favorable for the proper dehydration of alcohol to form ether?
a. Excess alcohol.
b. Good temperature control during reaction.
) Presence of bulky alkyl groups in the alcohol.
d. Presence of protic acids.
12) (1.5 pts) Which of the following is the least reactive functional group?
a. Alcohols
b. Aldehydes
@ Ethers
d. Ketones
