a)
Interpretation:
The products formed and the mechanism by which they are formed when 3-methoxypentane is treated with HBr is to be given.
Concept introduction:
Ethers are cleaved by strong acids. The cleavage takes place either by SN1 or SN2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single
To give:
The products formed and the mechanism by which it/they is/are formed when 3-methoxypentane is treated with HBr.
Answer to Problem 23MP
The products formed when 3-methoxypentane is treated with HBr are 3-pentanol and methyl bromide.
The mechanism of their formation is given below.
Explanation of Solution
The ether given has a secondary carbon and a primary carbon attached to the oxygen. The acid cleavage of the ether can take place through SN2 mechanism. The Br- attacks the protonated ether at the less hindered side to yield 3-pentanol and methyl bromide.
The products formed when 3-methoxypentane is treated with HBr are 3-pentanol and methyl bromide.
The mechanism of their formation is given below.
b)
Interpretation:
The products formed and the mechanism by which they are formed when ethyl isopropyl ether is treated with HI are to be given.
Concept introduction:
Ethers are cleaved by strong acids. The cleavage takes place either by SN1 or SN2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by SN1 or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.
To give:
The products formed and the mechanism by which they are formed when ethyl isopropyl ether is treated with HI.
Answer to Problem 23MP
The products formed when ethyl isopropyl ether is treated with HBr are 2-propanol and methyl iodide.
The mechanism of their formation is given below.
Explanation of Solution
The ether given has a secondary carbon and a primary carbon attached to the oxygen. The acid cleavage of the ether can take place through SN2 mechanism. The I- ion attacks the protonated ether at the less hindered side to yield 2-propanol and methyl iodide.
The products formed when ethyl isopropyl ether is treated with HBr are 2-propanol and methyl iodide.
The mechanism of their formation is given below.
c)
Interpretation:
The products formed and the mechanism by which they are formed when ethyl phenyl ether is treated with HBr is to be given.
Concept introduction:
Ethers are cleaved by strong acids. The cleavage takes place either by SN1 or SN2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by SN1 or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.
To give:
The products formed and the mechanism by which they are formed when ethyl phenyl ether is treated with HBr.
Answer to Problem 23MP
The products formed when ethyl phenyl ether is treated with HBr are phenol and ethyl iodide.
The mechanism of their formation is given below.
Explanation of Solution
The ether given has a benzene ring and a methyl group attached to the oxygen. The acid cleavage of the ether can take place through SN2 mechanism. The Br- ion attacks the protonated ether at the less hindered side to yield phenol and ethyl bromide.
The products formed when ethyl phenyl ether is treated with HBr are phenol and ethyl iodide.
The mechanism of their formation is given below.
d)
Interpretation:
The products formed and the mechanism by which they are formed when cyclopentyl propyl ether is treated with HI are to be given.
Concept introduction:
Ethers are cleaved by strong acids. The cleavage takes place either by SN1 or SN2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN2mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by SN1 or E1 mechanism because these can produce a stable carbocations yielding alkenes and alcohols.
To give:
The products formed and the mechanism by which they are formed when cyclopentyl propyl ether is treated with HI.
Answer to Problem 23MP
The products formed when cyclopentyl propyl ether is treated with HI are cyclopentanol and 1-iodopropane.
The mechanism of their formation is given below.
Explanation of Solution
The ether given has a secondary carbon and a primary carbon attached to the oxygen. The acid cleavage of the ether can take place through SN2 mechanism. The I- ion attacks the protonated ether at the less hindered side to yield cyclopentanol and 1-iodopropane.
The products formed when cyclopentyl propyl ether is treated with HI are cyclopentanol and 1-bromopropane.
The mechanism of their formation is given below.
All the reactions, (a), (b), (c) and (d) take place following SN2 mechanism and the attack of the halide ion on the protonated
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Chapter 18 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- Hi!! Please provide a solution that is handwritten. Ensure all figures, reaction mechanisms (with arrows and lone pairs please!!), and structures are clearly drawn to illustrate the synthesis of the product as per the standards of a third year organic chemistry course. ****the solution must include all steps, mechanisms, and intermediate structures as required. Please hand-draw the mechanisms and structures to support your explanation. Don’t give me AI-generated diagrams or text-based explanations, no wordy explanations on how to draw the structures I need help with the exact mechanism hand drawn by you!!! I am reposting this—ensure all parts of the question are straightforward and clear or please let another expert handle it thanks!!arrow_forwardHi!! Please provide a solution that is handwritten. Ensure all figures, reaction mechanisms (with arrows and lone pairs please!!), and structures are clearly drawn to illustrate the synthesis of the product as per the standards of a third year organic chemistry course. ****the solution must include all steps, mechanisms, and intermediate structures as required. Please hand-draw the mechanisms and structures to support your explanation. Don’t give me AI-generated diagrams or text-based explanations, no wordy explanations on how to draw the structures I need help with the exact mechanism hand drawn by you!!! I am reposting this—ensure all parts of the question are straightforward and clear or please let another expert handle it thanks!!arrow_forward. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B 2°C. +2°C. < cleavage Bond A • CH3 + 26. t cleavage 2°C• +3°C• Bond C Cleavage CH3 ZC '2°C. 26. E Strongest 3°C. 2C. Gund Largest BDE weakest bond In that molecule a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest C bond Produces A Weakest Bond Most Strongest Bond Stable radical Strongest Gund produces least stable radicals b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. 人 8°C. formed in bound C cleavage ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. methyl radical •CH3 formed in bund A Cleavagearrow_forward
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Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning