PRELAB EXERCISE: Predict the outcomes of the two sets of experiments to be carried out with the 11 halides used in this chapter. Group 1: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, and bromobenzene Group 2: 1-chlorobutane, 2-chloro-2-methylpropane, 1-chloro-2-butene Group 3: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane
PRELAB EXERCISE: Predict the outcomes of the two sets of experiments to be carried out with the 11 halides used in this chapter. Group 1: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, and bromobenzene Group 2: 1-chlorobutane, 2-chloro-2-methylpropane, 1-chloro-2-butene Group 3: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
Problem 18CTQ
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PRELAB EXERCISE: Predict the outcomes of the two sets of experiments to be carried out with the 11 halides used in this chapter (image attached)
for the first set of experiments, the solvent used is sodium iodide in acetone
for the second one it is ethnaloic silver nitrate
![Bromobenzene
bp 156°C
bp 68°C (trans)
Br
CH₂CH₂CHCH,
2-Bromobutane
bp 91°C
1-Chloro-2-methylpropane
bp 68-69°C
CH3
H₂C-C-Br
CH3
2-Bromo-2-methylpropane
bp 71-73°C
Once all of the halides have been placed into labeled tubes or vials, arrange them
into the following groupings:
Group 1: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, and
bromobenzene
Group 2: 1-chlorobutane, 2-chloro-2-methylpropane, 1-chloro-2-butene
Group 3: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane
When you perform experiments on these halides, be sure to do them in the
order in which they appear in their group lists in order to observe trends and make
conclusions about the reactivity of each halide within its respective group.
To each tube of each group, rapidly add 1 mL of an 18% solution of sodium
iodide in acetone, stopper each tube, mix the contents thoroughly, and note the
time. Note the time of first appearance of any precipitate. If no reaction occurs
within about 5 minutes, place those tubes in a 50°C water bath and watch for any
reaction over the next 5 or 6 minutes.
Empty the tubes, rinse them with ethanol, place the same amount of each of
the alkyl halides in each tube as in the first part of the experiment and organize
them by the groupings described above. Add 1 mL of 1% ethanolic silver nitrate
solution to each tube, mix the contents well, and note the time of addition as well
as the time of appearance of the first traces of any precipitate. If a precipitate does
not appear in 5 minutes, heat the tubes containing these unreactive halides in a
50°C water bath for 5 to 6 minutes and watch for any reaction.
To test the effect of solvent on the rate of S1 reactivity, compare the time
needed for a precipitate to appear when 2-chlorobutane is treated with a 1% ethano-
lic silver nitrate solution, and when treated with 1% silver nitrate in a mixture of
50% ethanol and 50% water.
In your analysis of the results from these experiments, consider the following
for both S1 and 52 conditions:
the nature of the leaving group (Cl vs. Br) in the 1-halobutanes
is compare simple primary, secondary, and tertiary](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F5f284ca5-c79e-4b73-917e-76c860ef7556%2F6f9b772f-059d-4dea-9db6-f37f846efd0a%2F9ibx02_processed.png&w=3840&q=75)
Transcribed Image Text:Bromobenzene
bp 156°C
bp 68°C (trans)
Br
CH₂CH₂CHCH,
2-Bromobutane
bp 91°C
1-Chloro-2-methylpropane
bp 68-69°C
CH3
H₂C-C-Br
CH3
2-Bromo-2-methylpropane
bp 71-73°C
Once all of the halides have been placed into labeled tubes or vials, arrange them
into the following groupings:
Group 1: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, and
bromobenzene
Group 2: 1-chlorobutane, 2-chloro-2-methylpropane, 1-chloro-2-butene
Group 3: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane
When you perform experiments on these halides, be sure to do them in the
order in which they appear in their group lists in order to observe trends and make
conclusions about the reactivity of each halide within its respective group.
To each tube of each group, rapidly add 1 mL of an 18% solution of sodium
iodide in acetone, stopper each tube, mix the contents thoroughly, and note the
time. Note the time of first appearance of any precipitate. If no reaction occurs
within about 5 minutes, place those tubes in a 50°C water bath and watch for any
reaction over the next 5 or 6 minutes.
Empty the tubes, rinse them with ethanol, place the same amount of each of
the alkyl halides in each tube as in the first part of the experiment and organize
them by the groupings described above. Add 1 mL of 1% ethanolic silver nitrate
solution to each tube, mix the contents well, and note the time of addition as well
as the time of appearance of the first traces of any precipitate. If a precipitate does
not appear in 5 minutes, heat the tubes containing these unreactive halides in a
50°C water bath for 5 to 6 minutes and watch for any reaction.
To test the effect of solvent on the rate of S1 reactivity, compare the time
needed for a precipitate to appear when 2-chlorobutane is treated with a 1% ethano-
lic silver nitrate solution, and when treated with 1% silver nitrate in a mixture of
50% ethanol and 50% water.
In your analysis of the results from these experiments, consider the following
for both S1 and 52 conditions:
the nature of the leaving group (Cl vs. Br) in the 1-halobutanes
is compare simple primary, secondary, and tertiary
![PRELAB EXERCISE: Predict the outcomes of the two sets of experiments
to be carried out with the 11 halides used in this chapter.
Group 1: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, and
bromobenzene
Group 2: 1-chlorobutane, 2-chloro-2-methylpropane, 1-chloro-2-butene
Group 3: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F5f284ca5-c79e-4b73-917e-76c860ef7556%2F6f9b772f-059d-4dea-9db6-f37f846efd0a%2Fmdgbxb_processed.png&w=3840&q=75)
Transcribed Image Text:PRELAB EXERCISE: Predict the outcomes of the two sets of experiments
to be carried out with the 11 halides used in this chapter.
Group 1: 1-bromobutane, 2-bromobutane, 2-bromo-2-methylpropane, and
bromobenzene
Group 2: 1-chlorobutane, 2-chloro-2-methylpropane, 1-chloro-2-butene
Group 3: 1-bromobutane, 2-bromobutane, 1-chlorobutane, 2-chlorobutane
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