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Consider the triple alcohol drawn below. It contains all three types (1º, 2º, and 3º) of alcohols (not counting methanol CH3OH). Note that all three O atoms must have two lone pairs of electrons, but these are not shown due to the limitations of my graphics program. OH OH OH la. Directly on the image above, label each chiral center with a “star” (*). 1b. The triple alcohol above is treated with excess HCl. Because there is more HCl than needed, all three alcohols will be converted to chloralkanes. That is, all three alcohol groups will be undergo nucleophilic substitution to form three chloroalkanes. Draw the structures of ALL resulting products (there will obviously be more than one structure). 3° alcohols react exclusively via the SNl mechanism, while 1° alcohols go exclusively via SN2. The textbook is a bit wishy-washy about 2° alcohols, so for the purpose of this HW, assume an SN1 mechanism. There is no need to indicate the absolute configurations on any of your structures, but make sure you clearly use solid wedge or broken/hatched wedge bonds as appropriate.

Consider the triple alcohol drawn below. It contains all three types (1º, 2º, and 3º) of alcohols (not counting methanol CH3OH). Note that all three O atoms must have two lone pairs of electrons, but these are not shown due to the limitations of my graphics program. OH OH OH la. Directly on the image above, label each chiral center with a “star” (*). 1b. The triple alcohol above is treated with excess HCl. Because there is more HCl than needed, all three alcohols will be converted to chloralkanes. That is, all three alcohol groups will be undergo nucleophilic substitution to form three chloroalkanes. Draw the structures of ALL resulting products (there will obviously be more than one structure). 3° alcohols react exclusively via the SNl mechanism, while 1° alcohols go exclusively via SN2. The textbook is a bit wishy-washy about 2° alcohols, so for the purpose of this HW, assume an SN1 mechanism. There is no need to indicate the absolute configurations on any of your structures, but make sure you clearly use solid wedge or broken/hatched wedge bonds as appropriate.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Consider the triple alcohol drawn below. It contains all three types (1º, 2º, and 3º) of alcohols (not counting methanol CH3OH). Note that all three O atoms must have two lone pairs of electrons, but these are not shown due to the limitations of my graphics program. OH LOH OH 1a. Directly on the image above, label each chiral center with a “star” (*). 1b. The triple alcohol above is treated with excess HCl. Because there is more HCl than needed, all three alcohols will be converted to chloralkanes. That is, all three alcohol groups will be undergo nucleophilic substitution to form three chloroalkanes. Draw the structures of ALL resulting products (there will obviously be more than one structure). 3° alcohols react exclusively via the SNl mechanism, while 1° alcohols go exclusively via SN2. The textbook is a bit wishy-washy about 2° alcohols, so for the purpose of this HW, assume an SN1 mechanism. There is no need to indicate the absolute configurations on any of your structures, but make sure you clearly use solid wedge or broken / hatched wedge bonds as appropriate.
Transcribed Image Text:Consider the triple alcohol drawn below. It contains all three types (1º, 2º, and 3º) of alcohols (not counting methanol CH3OH). Note that all three O atoms must have two lone pairs of electrons, but these are not shown due to the limitations of my graphics program. OH LOH OH 1a. Directly on the image above, label each chiral center with a “star” (*). 1b. The triple alcohol above is treated with excess HCl. Because there is more HCl than needed, all three alcohols will be converted to chloralkanes. That is, all three alcohol groups will be undergo nucleophilic substitution to form three chloroalkanes. Draw the structures of ALL resulting products (there will obviously be more than one structure). 3° alcohols react exclusively via the SNl mechanism, while 1° alcohols go exclusively via SN2. The textbook is a bit wishy-washy about 2° alcohols, so for the purpose of this HW, assume an SN1 mechanism. There is no need to indicate the absolute configurations on any of your structures, but make sure you clearly use solid wedge or broken / hatched wedge bonds as appropriate.
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