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a)
Interpretation:
A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl3, is to be proposed. The regiochemistry of the elimination is also to be explained.
Concept introduction:
The dehydration of alcohols to
To propose:
A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl3 is to be proposed.
To explain:
The regiochemistry of the elimination reaction.
b)
Interpretation:
A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl3, is to be proposed. The regiochemistry of the elimination is also to be explained.
Concept introduction:
The dehydration of alcohols to alkenes in the presence of POCl3 follows E2 mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl2, when treated with POCl3. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E2 mechanism). The removal of the proton and –OPOCl2 occurs simultaneously in a single step to yield the alkene as the product.
To propose:
A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl3, is to be proposed.
To explain:
The regiochemistry of the elimination reaction.
c)
Interpretation:
A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl3, is to be proposed. The regiochemistry of the elimination is also to be explained.
Concept introduction:
The dehydration of alcohols to alkenes in the presence of POCl3 follows E2 mechanism. The –OH group is converted into a better leaving group dichlorophosphate, –OPOCl2, when treated with POCl3. Pyridine used as solvent is also a base and it removes a proton arranged anti to the leaving group from the β carbon (requirement for E2 mechanism). The removal of the proton and –OPOCl2 occurs simultaneously in a single step to yield the alkene as the product.
To propose:
A mechanism using curved arrows, for the conversion of alcohol given into the corresponding alkene by treating with POCl3, is to be proposed.
To explain:
The regiochemistry of the elimination reaction.
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Chapter 17 Solutions
Organic Chemistry
- Nonearrow_forwardNonearrow_forwardman Campus Depa (a) Draw the three products (constitutional isomers) obtained when 2-methyl-3-hexene reacts with water and a trace of H2SO4. Hint: one product forms as the result of a 1,2-hydride shift. (1.5 pts) This is the acid-catalyzed alkene hydration reaction.arrow_forward
- (6 pts - 2 pts each part) Although we focused our discussion on hydrogen light emission, all elements have distinctive emission spectra. Sodium (Na) is famous for its spectrum being dominated by two yellow emission lines at 589.0 and 589.6 nm, respectively. These lines result from electrons relaxing to the 3s subshell. a. What is the photon energy (in J) for one of these emission lines? Show your work. b. To what electronic transition in hydrogen is this photon energy closest to? Justify your answer-you shouldn't need to do numerical calculations. c. Consider the 3s subshell energy for Na - use 0 eV as the reference point for n=∞. What is the energy of the subshell that the electron relaxes from? Choose the same emission line that you did for part (a) and show your work.arrow_forwardNonearrow_forward(9 Pts) In one of the two Rare Earth element rows of the periodic table, identify an exception to the general ionization energy (IE) trend. For the two elements involved, answer the following questions. Be sure to cite sources for all physical data that you use. a. (2 pts) Identify the two elements and write their electronic configurations. b. (2 pts) Based on their configurations, propose a reason for the IE trend exception. c. (5 pts) Calculate effective nuclear charges for the last electron in each element and the Allred-Rochow electronegativity values for the two elements. Can any of these values explain the IE trend exception? Explain how (not) - include a description of how IE relates to electronegativity.arrow_forward
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