Sunteți pe pagina 1din 4

CCB 1013 ORGANIC CHEMISTRY ASSIGNMENT #1

Instructions: Answer ALL questions. There are FOUR (4) pages. Where applicable, show clearly steps taken in arriving at the solutions. 1. Consider the SN2 reaction of 1-chloro-5-methylhexane with CN ion.
NaCN NaCl

Cl

CN

Assuming no other changes, what effect on the rate would result from simultaneously doubling the concentrations of both 1-chloro-5[1 mark] methylhexane and CN ion?

2.

What product(s) would you expect to obtain from the following SN2 reaction? [1 mark]
H H

CH3ONa ? CH3OH

CH3

Br

3.

Keeping in mind that carbocations have a trigonal planar structure, (a) write a structure for the carbocation intermediate and (b) write structures for the alcohol (or alcohols) that you would expect from the following reaction: [3 marks]
I
(CH3)3C

CH3

4.

Which of the following alkyl halides is most likely to undergo substitution by an SN1 mechanism? Explain your answer. [2 marks]

Br

Br CH3

Br

(a) 5.

(b)

(c)

Which alkyl halide would you expect to react more rapidly by an SN2 mechanism? Explain your answer. [6 marks] (a)
Cl
Cl

or
Cl

(b)
Cl

or

(c) 6.

or

Cl

Your task is to prepare styrene by one of the following reactions. Which reaction would you choose to give the better yield of styrene? Explain your answer. [3 marks] (a)
Br
KOH EtOH,

(b)
Br
KOH EtOH,

7.

Which SN1 reaction of each pair would you expect to take place more rapidly? Explain your answer. [6 marks] (a) (1)
Cl

H O

OH

HCl

or (2)
Br

H O

OH

HBr

(b)

(1) (1.0M) EtO 1.0


Cl

EtOH

Cl
OEt

or (2) Cl (c) (1)


Cl

(2.0M) EtO 1.0

EtOH

Cl
OEt

H O

OH

HCl

or (2)
Cl OH

H O

HCl

8.

Which product(s) would you expect to obtain from each of the following reactions? In each part give the mechanism (SN1, SN2, E1, or E2) by which each product is formed and predict the relative amount of each product (i.e., would the product be the only product, the major product, a minor product, etc.?). [12 marks] (a) (b) (c)
Br

EtO EtOH, 50 t-BuOK t-BuOH, 50

Br

MeO MeOH, 50 Br
Cl

(d)
t-Bu

I acetone, 50

9.

What is the effect of each of the following on the SN1 reaction between t-butyl chloride and water? [4 marks] (a) Increasing the concentration of water (b) Performing the reaction in hexanes (c) Decreasing the concentration of t-butyl chloride (d) Adding acetone as cosolvent The reaction of chloroethane with water in the gas phase to produce ethanol and hydrogen chloride has 26.6 kJ mol and 4.81 J K mol at 25. [7 marks] (a) Which of these terms, if either, favors the reaction going to completion? (b) Calculate for the reaction. What can you now say about whether the reaction will proceed to completion? (c) Calculate the equilibrium constant for the reaction. (d) In aqueous solution the equilibrium constant is very much larger than the calculated value in (c). How can you account for this fact? [Deadline: 25th June 2013 (Tues), 12 noon]
4

10.

S-ar putea să vă placă și