
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
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- Would the following organic synthesis occur in one step? Add any missing products, required catalysts, inorganic reagents, and other important conditions. Please include a detailed explanation and drawings showing how the reaction may occur in one step.arrow_forward(a) Sketch the 'H NMR of the following chemical including the approximate chemical shifts, the multiplicity (splitting) of all signals and the integration (b) How many signals would you expect in the 13C NMR? CH3arrow_forwardDraw the Show the major and minor product(s) for the following reaction mechanisms for both reactions and show all resonance structures for any Explain why the major product is favoured? intermediates H-Brarrow_forward
- 3. Draw ALL THE POSSBILE PRODUCTS AND THE MECHANISMS WITH ALL RESONANCE STRUCTURES. Explain using the resonance structures why the major product(s) are formed over the minor product(s). H₂SO4, HONO CHarrow_forward7. Provide the product(s), starting material(s) and/or condition(s) required for the No mechanisms required. below reaction HO + H-I CI FO Br2, FeBr3 O I-Oarrow_forward6. Design the most efficient synthesis of the following product starting from phenot Provide the reaction conditions for each step (more than one step is required) and explain the selectivity of each reaction. NO MECHANISMS ARE REQUIRED. OH step(s) CIarrow_forward
- What is the skeletal structure of the product of the following organic reaction?arrow_forwardIf a reaction occurs, what would be the major products? Please include a detailed explanation as well as a drawing showing how the reaction occurs and what the final product is.arrow_forwardWhat is the major organic product of the following nucleophilic acyl substitution reaction of an acid chloride below?arrow_forward
