Substitution Nucleophilic Reactions of Alkyl Halides

Organic Chemistry Virtual Lab (Guide)

Summer I 2021

Objectives

(a) To understand the different types of Substitution Reactions: SN1 and SN2
(b) To investigate the effects of leaving groups on the rate of substitution reactions.
(c) To investigate the effects of the alkyl halide’s structure on the rate of substitution
reactions
Introduction

The prelab lecture is provided below. For additional information, review Chapter 17 of
the lab manual

Link to the Prelab lecture: https://drive.google.com/file/d/1ViMd4Tdw8lp54Ptkh-

sJvvDoSzG1TajC/view?usp=sharing
The structures/names of all alkyl halides used are included in the lab manual
General reaction equation

R X + Nu R Nu + X

Alkyl halide Nucleophile

Experimental Procedure
The experimental procedure (for this lab) is described in Chapter 17. 
Below is the summary of the two reaction conditions used:

Reaction Conditions (RC) 1: Sodium Iodide in Acetone

To each tube containing a small amount of each group, add 1 ml of an 18% solution of
sodium iodide in acetone, stopper each tube, and mix the content thoroughly, noting the
time of the first appearance of any precipitate (PPT). If no reaction (PPT) occurred after
5-10 mins, place the tube in a 50°C water bath and observe any chemical reactions over
the next 5-10 mins.

Reaction Conditions (RC) 2: Ethanolic Silver Nitrate Solution

To each tube containing a small amount of each group, add 1 ml of 1% ethanolic silver
nitrate solution, and mix the content thoroughly, noting the time of the first appearance of
any precipitate (PPT). If no reaction (PPT) occurred after 5-10 mins, place the tube in a
50°C water bath and observe any chemical reactions over the next 5-10 mins.

Keywords: RC = Reaction Conditions; PPT = Precipitate; rt = room temperature; warm =

warm water bath

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Substitution Nucleophilic Reactions of Alkyl Halides
Organic Chemistry Virtual Lab (Guide)
Summer I 2021

Results

The table below summarizes the observations of each alkyl halide's reaction (using either
conditions 1 or 2) with the nucleophile. PPT means that the reaction occurred, and one of
the products precipitated out of solution; note how fast each reaction occurred based on
the time. Each group (1 – 3) is as described in the lab manual.

Table of Results

Group 1            

R R
Alkyl Halides (RX) C Observations C Observations

rt 1-bromobutane 1 PPT formed in 3 mins 2 No PPT formed

warm 1-bromobutane 1 Not Needed   2 No PPT formed

rt 2-bromobutane 1 PPT formed in 7 mins 2 No PPT formed

warm 2-bromobutane 1 PPT formed in 4 mins   2 PPT formed in 5 min

2-bromo-2-
rt methylpropane 1 No PPT formed 2 PPT formed in 2 mins

2-bromo-2-
warm methylpropane 1 PPT formed in 10 min   2 Not Needed

rt bromobenzene 1 No PPT formed 2 No PPT formed

warm bromobenzene 1 No PPT formed   2 No PPT formed

Group 2            

R R
Alkyl Halides (RX) C Observations C Observations

PPT formed in 10
rt 1-chlorobutane 1 mins 2 No PPT formed

warm 1-chlorobutane 1 PPT formed in 6 mins   2 No PPT formed

rt 2-chloro-2-methylpropane 1 No PPT formed 2 PPT formed in 5 mins

warm 2-chloro-2-methylpropane 1 No PPT formed   2 Not Needed

rt 1-chloro-2-butene 1 PPT formed in 3 mins 2 PPT formed in 3 mins

warm 1-chloro-2-butene 1 Not Needed   2 Not Needed

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Substitution Nucleophilic Reactions of Alkyl Halides
Organic Chemistry Virtual Lab (Guide)
Summer I 2021

Group 3            

R R
Alkyl Halides (RX) C Observations C Observations

rt 1-bromobutane 1 PPT formed in 3 mins 2 No PPT formed

warm 1-bromobutane 1 Not Needed   2 No PPT formed

rt 2-bromobutane 1 PPT formed in 7 mins 2 No PPT formed

warm 2-bromobutane 1 PPT formed in 4 mins   2 PPT formed in 5 min

PPT formed in 10
rt 1-chlorobutane 1 mins 2 No PPT formed

warm 1-chlorobutane 1 PPT formed in 6 mins   2 No PPT formed

rt 2-chlorobutane 1 PPT formed in 8 mins 2 No PPT formed

PPT formed in 10
warm 2-chlorobutane 1 PPT formed in 5 mins   2 mins

Discussion

Examine the data in the results and address the three objectives of this lab. Include
specific reaction examples from the table.

Questions

Answer questions 1 and 2

Note: Include all sections (except Chemical Equation) of the lab report. See the example
in the syllabus.