Observe
each of the alkyl halides listed below as they react with a solution of
sodium iodide in acetone. Record the appearance of any precipitate and
the approximate time it formed.
*Some reactions may be more pronounced than others. The precipitate may
be a particulate that settles to the bottom of the test tube, a bright
white suspended mixture, or may only form a fine haze in the solution.
Describe the extent of the reaction you observe - these details will
help you in your post-lab discussion.* Note that a color change without
the formation of precipitate is not an indication of a substitution
reaction.
Which substrate would you like to test first?
[[1-chlorobutane]]
[[1-bromobutane]]
[[2-chlorobutane]]
[[2-chloro-2-methylpropane]]
[[3-chloro-1-butene]]
[[1-chloro-2-methylpropane]]
[[chlorobenzene]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
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Player"></iframe>
What would you like to do next?
[[Heat 1-chlorobutane]]
[[Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_6zs9g2jq&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_5x87iw9m"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[Heat 1-bromobutane]]
[[Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_mlrtlsb4&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_hcdhkx8r"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[Heat 2-chlorobutane]]
[[Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_pg4588cn&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_vwr5l1vb"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[Heat 2-chloro-2-methylpropane]]
[[Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_vw2fbwcj&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_ppcdsfbn"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[Heat 3-chloro-1-butene]]
[[Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_gg3vyoux&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_biu61lpl"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[Heat 1-chloro-2-methylpropane]]
[[Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_ngzqtsb3&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_hje2kz6i"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[Heat chlorobenzene]]
[[Test another substrate]]This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_rpsdb5e3&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_cfurv84i"
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Player"></iframe>
All set? [[Test another substrate]]Continue
to observe each of the alkyl halides listed below as they react with a
solution of sodium iodide in acetone. Record the appearance of any
precipitate and the approximate time it formed. You are also welcome to
revisit any of the substrates during this experience.
Which substrate would you like to test next?
[[1-chlorobutane]]
[[1-bromobutane]]
[[2-chlorobutane]]
[[2-chloro-2-methylpropane]]
[[3-chloro-1-butene]]
[[1-chloro-2-methylpropane]]
[[chlorobenzene]]
Once you have completed your observations of these substrates treated
with sodium iodide in acetone, you may move on to the second set of
tests using silver nitrate in ethanol.
[[Continue with the silver nitrate in ethanol tests]]Does
this substrate need to be heated? Was there no clear precipitation
reaction? Let's look at that room temperature video of [[1-bromobutane]]
again...This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_8gnt6s6t&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_f51c7te8"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[Test another substrate]] This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_euqlg99p&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_rsnh33l0"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[Test another substrate]] This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_sc7h9s4d&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_gqc8ulnv"
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Player"></iframe>
All set? [[Test another substrate]] This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_j3ycvlf1&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_tqz0zl67"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[Test another substrate]] This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_gf5vjoyd&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_oh6b6788"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[Test another substrate]] Observe
each of the alkyl halides listed below as they react with a solution of
silver nitrate in ethanol. Record the appearance of any precipitate and
the approximate time it formed.
*Remember: Some reactions may be more pronounced than others. The
precipitate may be a particulate that settles to the bottom of the test
tube, a bright white suspended mixture, or may only form a fine haze in
the solution. Describe the extent of the reaction you observe - these
details will help you in your post-lab discussion.* Note that a color
change without the formation of precipitate is not an indication of a
substitution reaction.
Which substrate would you like to test first?
[[ 1-chlorobutane]]
[[ 1-bromobutane]]
[[ 2-chlorobutane]]
[[ 2-chloro-2-methylpropane]]
[[ 3-chloro-1-butene]]
[[ 1-chloro-2-methylpropane]]
[[ chlorobenzene]]''Experiment
6:
REACTIONS OF ALKYL HALIDES IN NUCLEOPHILIC SUBSTITUTION REACTIONS''
*Twine created by Dr. Samantha Reynolds, UNH Manchester*
In this experiment, you will explore the reactivity of several alkyl
halides (and one aryl halide) under both S<sub>N</sub>1 and
S<sub>N</sub>2 conditions. Two nucleophilic reagents will be
used: a solution of sodium iodide, NaI, in acetone, and a solution of
silver nitrate, AgNO<sub>3</sub>, in ethanol.
[[Let's begin with the sodium iodide in acetone tests]] If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_osk9o6f4&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_fss8xc9n"
width="400" height="285" allowfullscreen webkitallowfullscreen
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allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat 1-chlorobutane]]
[[ Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_xk0nviz3&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_kmhxcvd5"
width="400" height="285" allowfullscreen webkitallowfullscreen
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sandbox="allow-forms allow-same-origin allow-scripts
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allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat 1-bromobutane]]
[[ Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_l6v3zci4&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_08lez4r3"
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allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat 2-chlorobutane]]
[[ Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_5bzcbw66&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_4z65vdkc"
width="400" height="285" allowfullscreen webkitallowfullscreen
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sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat 2-chloro-2-methylpropane]]
[[ Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_qqh04b38&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_u2pws8ne"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat 3-chloro-1-butene]]
[[ Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_psr92lke&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_12g6fr65"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat 1-chloro-2-methylpropane]]
[[ Test another substrate]]If
you observe a reaction at room temperature, you do not need to watch as
the test tube is heated.
If you do not observe any reaction after five minutes at room
temperature, note this in your observations and watch as the solution is
heated in a warm water bath.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_2mzwqrnd&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_t7844be9"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
What would you like to do next?
[[ Heat chlorobenzene]]
[[ Test another substrate]]This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_ua82smgb&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_hk4h5o5o"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[ Test another substrate]]Continue
to observe each of the alkyl halides listed below as they react with a
solution of silver nitrate in ethanol. Record the appearance of any
precipitate and the approximate time it formed. You are also welcome to
revisit any of the substrates during this experience.
Which substrate would you like to test next?
[[ 1-chlorobutane]]
[[ 1-bromobutane]]
[[ 2-chlorobutane]]
[[ 2-chloro-2-methylpropane]]
[[ 3-chloro-1-butene]]
[[ 1-chloro-2-methylpropane]]
[[ chlorobenzene]]
Once you have completed your observations of these substrates treated
with sodium iodide in acetone, your lab experience for this experiment
is complete.Does
this substrate need to be heated? Was there no clear precipitation
reaction? Let's look at that room temperature video of [[
1-bromobutane]] again...This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_a3xefykp&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_q6mkj035"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[ Test another substrate]] Does
this substrate need to be heated? Was there no clear precipitation
reaction? Let's look at that room temperature video of [[
2-chloro-2-methylpropane]] again...Does
this substrate need to be heated? Was there no clear precipitation
reaction? Let's look at that room temperature video of [[
3-chloro-1-butene]] again...This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_rpbioauc&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_g466o4t3"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[ Test another substrate]] This
video begins only a few seconds after the test tubes have been
positioned in the warm water bath.
The temperature of the water is approximately 50
<sup>o</sup>C.
If you do not observe a reaction after five minutes of heating, record
"no reaction" for this substrate, and continue to another test.
<iframe id="kaltura_player"
src="https://cdnapisec.kaltura.com/p/505811/sp/50581100/embedIframeJs/uiconf_id/30754302/partner_id/505811?iframeembed=true&playerId=kaltura_player&entry_id=1_0a2avxui&flashvars[streamerType]=auto&flashvars[localizationCode]=en&flashvars[leadWithHTML5]=true&flashvars[sideBarContainer.plugin]=true&flashvars[sideBarContainer.position]=left&flashvars[sideBarContainer.clickToClose]=true&flashvars[chapters.plugin]=true&flashvars[chapters.layout]=vertical&flashvars[chapters.thumbnailRotator]=false&flashvars[streamSelector.plugin]=true&flashvars[EmbedPlayer.SpinnerTarget]=videoHolder&flashvars[dualScreen.plugin]=true&flashvars[hotspots.plugin]=1&flashvars[Kaltura.addCrossoriginToIframe]=true&&wid=1_31q1rmkf"
width="400" height="285" allowfullscreen webkitallowfullscreen
mozAllowFullScreen allow="autoplay *; fullscreen *; encrypted-media *"
sandbox="allow-forms allow-same-origin allow-scripts
allow-top-navigation allow-pointer-lock allow-popups allow-modals
allow-orientation-lock allow-popups-to-escape-sandbox allow-presentation
allow-top-navigation-by-user-activation" frameborder="0" title="Kaltura
Player"></iframe>
All set? [[ Test another substrate]]
↶↷Experiment 6:
REACTIONS OF ALKYL HALIDES IN NUCLEOPHILIC SUBSTITUTION REACTIONS
Twine created by Dr. Samantha Reynolds, UNH Manchester
In this experiment, you will explore the reactivity of several alkyl halides (and one aryl halide) under both SN1 and SN2
conditions. Two nucleophilic reagents will be used: a solution of
sodium iodide, NaI, in acetone, and a solution of silver nitrate, AgNO3, in ethanol.
Let's begin with the sodium iodide in acetone tests