CHEM 2114
Practice Problems – Unit 4
1.
Name
the following compounds:
2.
Draw
the following compounds:
a. 1-fluoro-5-methylhexane
b. 2-bromo-4,5-dimethylheptane
c. (2S, 4R)-2-bromo-4-methylhexane
d. (1S, 2R, 4S)-1,2-dibromo-4-methylcyclohexane
3.
Which
one in each pair has the lower BP?
4.
Which
compound in each pair has higher density?
a. dichloromethane or water
b. water or hexane
c. hexane or chloroform
5.
Complete
the following reactions by drawing the product.
6.
Complete
the following reactions by supplying the appropriate reagents and conditions.
7.
Draw
the structure of the major substitution
product formed in the following reactions:
8.
What
reagents would you use to accomplish the following reactions?
9.
Draw
the mechanism for each of the following:
a.
the
reaction shown in 7a
b.
the
reaction shown in 7d
c.
the
reaction shown in 8b
10.
Indicate
whether the following reactions occur via an SN1 or SN2
mechanism.
11.
Which
of the following alkyl halides are good substrates for an SN1
reaction? For an SN2
reaction?
a.
1-bromo-4-methylpentane
b.
1-bromo-2,2-dimethylpropane
c.
1-bromo-1-methylcyclohexane
d.
Methyl
iodide
e.
Benzyl
bromide (bromophenylmethane)
f.
3-bromo-3-methylpentane
12.
Identify
each alkyl halide in question 11 as primary, secondary, tertiary, allylic,
benzylic, vinyl, or methyl.
13.
Draw
Lewis structures for the following and identify which ones are potential
nucleophiles.
a. CH3CH2NH2 e. CH3SH
b. water f. sodium cyanide
c. methyl bromide g. HC2-
d. potassium iodide h. chlorine
14.
Draw
the mechanism for the following reactions.
15.
Draw
the mechanism for the following reactions.
16.
Each
of the following reactions forms multiple products. Draw the structures of all possible products
and label them as major or minor.
17.
Predict
the major elimination reaction product:
18.
Draw
the mechanism for the reaction shown in question 16a. Remember to account for all products formed.
19.
Draw
the mechanism for the reaction shown in question 17c.
20.
Consider
the reaction shown in 17c. What happens
to the rate of the reaction when (a) [NaOCH3] is doubled; (b) [RX]
is tripled?
21.
Consider
the reaction shown in 14a. What happens
to the rate of the reaction when (a) [CH3OH] is doubled; (b) [RX] is
tripled?
22.
Explain
why the following reactions do not occur.
23.
Which
is the stronger nucleophile?
24.
Which
of the following are good leaving groups?
25.
Each
of the following reactions can be accomplished in 2 steps. Complete the synthetic scheme by filling in
the appropriate reagents and intermediate product. (Note:
The intermediate product will never
be a reactive intermediate.)
26.
Draw
the major product formed:
27.
Draw
the mechanism for the reaction shown in question 26.
28.
Identify
all asymmetric carbons present in the following compound.
29.
Identify
the relationship between the following pairs of compounds.
30.
A
student reacted 1-bromo-2-methylcyclohexane with sodium hydroxide in DMF at
room temperature. After isolation and
purification, the following IR spectrum was obtained for the product. Draw the structure of the product obtained.
31.
A
student reacted 2-bromo-3,3-dimethylhexane with sodium
methoxide in methanol at 65oC for 3 hours. After isolating and purifying the product,
she obtained a compound with the following spectrum. Draw a reasonable structure for the product.
