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Raheel Hussein
May 13, 2021
Experiment 11 Sn1 and Sn2 Reactions
I.
Introduction[7]
The purpose of this experiment is to test some aspects of nucleophilic
substitution reaction mechanisms. From there, the goal is to be able to identify the
effects of substitution patterns on nucleophilic substitution reactions as well as the
effects of solvent on nucleophilic substitution reactions. For this lab activity, would
need the review or refresh on the topic of nucleophile subsitution of alkyl halides.
II.
Safety
In this section, the essential information regarding the substances or mixtures
utilized in this experiment is generated from reference Material Safety Data Sheets
(see Citations). This is to ensure that proper handling in working with these
chemicals is observed.
1. 1-Bromobutane (C4H9Br)[1] and 2-Bromobutane (C4H9Br)[3]
NFPA Ratings:
Health Hazard – 2
Flammability
–3
Reactivity
–0
Other Hazards:
Combustible,
Inhalation
(Causes
respiratory
tract
irritation), Skin (When contacted, wash with soap and water), Eyes (Immediately
flush eyes with plenty of water), Ingestion (Do NOT induce vomiting unless directed
to do so by medical personnel)
2. 1-Chlorobutane (C4H9Cl)[2] and 2-Chlorobutane (C4H9Cl)[4]
NFPA Ratings:
Health Hazard – 2
Reactivity
Other Hazards:
Flammability – 3
–0
Combustible,
Inhalation
(Causes
respiratory tract irritation), Skin (When contacted, wash with soap and water), Eyes
(Immediately flush eyes with plenty of water), Ingestion (Do NOT induce vomiting
unless directed to do so by medical personnel), Wear personal protective equipment
3. 2-Chloro-2-methylpropane ((CH3)3CCl)[8]
NFPA Ratings:
Health Hazard – 2
Reactivity
Other Hazards:
Flammability – 3
–0
Combustible,
Inhalation
(Causes
respiratory
tract
irritation), Skin (When contacted, wash with soap and water), Eyes (Immediately
flush eyes with plenty of water), Ingestion (Do NOT induce vomiting unless directed
to do so by medical personnel), Wear personal protective equipment
4. Acetone (CH3)2CO[9]
NFPA Ratings:
Health Hazard – 1
Reactivity
Other Hazards:
Flammability – 3
–0
Combustible, Skin (When contacted, wash with soap and
water), Eyes (Immediately flush eyes with plenty of water), Ingestion (Very
hazardous when ingested and inhaled. Do NOT induce vomiting unless directed to
do so by medical personnel), Toxic to lungs, nervous system, and mucous
membranes when exposed for too long.
5. Silver Nitrate (AgNO3)[10]
NFPA Ratings:
Health Hazard – 3
Reactivity
Other Hazards:
–2
Flammability – 1
Specific – OX
Material contains oxidizing properties, Flammable,
Hazardous to Skin (When contacted, wash with soap and water), Eyes (Immediately
flush eyes with plenty of water), Ingestion (Very hazardous when ingested and
inhaled. Do NOT induce vomiting unless directed to do so by medical personnel)
III.
Experimental Procedure[5. 7]
1. The experiment should be performed in a well-ventilated area. The
experiment will focus on nucleophilic substitution of polar priotic and polar
apriotic solvents.
2. For polar priotic solvents, obtain 5 clean, dry test tubes. Label these with the
following names of compounds: 1-bromobutane, 1-chlorobutane, 2bromobutane, 2-chlorobutane, and 2-chloro-2-methylpropane.
3. Add 2 mL of a 0.1 M silver nitrate in ethanol solution to each test tube, then
add 1 drop of each alkyl halide to the correct test tube.
4. Next, shake the test tubes carefully. The goal is to gain a precipitation reaction.
5. Record the time required for the appearance of the first sign of cloudiness.
6. If, after 10 minutes, relative order of reactivity cannot be established, put the
test tubes in a warm water bath for up to 10 minutes.
7. Record the result even if the case is after the time has elapsed, no reaction
occurs.
8. Conduct the same process but this time, for polar apriotic solvents.
9. Add 1 mL of a 15% sodium iodide in acetone solution to each test tube.
10.Then, add 2 drops of each alkyl halide to the correct test tube. Shake the test
tube carefully. Observe and look for a precipitation reaction.
11.Record the time required for appearance of the first sign of cloudiness (the
reaction is not a discoloration without precipitate).
12.You can then place the test tubes in a warm water bath if an order of reactivity
is not established after 10 minutes. Longest time could be 20 minutes total.
After this time has passed, record the final results.
IV.
Observations and Results
The Table 1 below shows the observations, properties to be considered, if a
precipitation formation has been recorded, and if an elevated temperature was
required.
Table 1. Table of Observations, Mechanism, and Reactions[5, 7]
Alkyl
Halide
Expected
Mechanism
NaI
1o since the C is ppt
Br
bonded
to
to AgNO3
EtOH
3 min
No rxn
1 formed No heat
another
C,
therefore
it
should
Time
React
Time
React
to Expected
Products if
Reaction
Occurs
I
O
follow
Sn2.
1o since the C is ppt
bonded
Cl
to
1 formed 3 min at RT
another
C,
therefore
it
should
follow Sn2.
5 min total
also
No rxn
I
2 min heat
O
Carbon
Br
with ppt
halogen
7 min total
ppt
3 min
I
is formed 3 min at RT formed
bonded
to
2
4 mi...