a)
Interpretation:
The products formed and the mechanism by which they are formed when tert-butyl ethyl 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
To give:
The products formed and the mechanism by which they are formed when tert-butyl ethyl ether is treated with HBr is to be given.
Answer to Problem 24MP
The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.
The mechanism by which they are formed is given below.
Explanation of Solution
The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide as the product.
The products formed when tert-butyl ethyl ether is treated with HBr are ethanol and tert-butylbromide.
The mechanism by which they are formed is given below.
b)
Interpretation:
The products formed and the mechanism by which they are formed when tert-butyl 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 tert-butyl phenyl ether is treated with HBr.
Answer to Problem 24MP
The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.
The mechanism by which they are formed is given below.
Explanation of Solution
The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates phenol to produce a stable tert-butyl carbocation. In the next step the bromide ion attacks the carbocation to yield tert-butyl bromide.
The products formed when tert-butyl phenyl ether is treated with HBr are phenol and tert-butyl bromide.
The mechanism by which they are formed is given below.
c)
Interpretation:
The products formed and the mechanism by which they are formed when tert-butyl isopropyl ether is treated with HI 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 tert-butyl isopropyl ether is treated with HI.
Answer to Problem 24MP
The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.
The mechanism by which they are formed is given below.
Explanation of Solution
The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates 2-propanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.
The products formed when tert-butyl isopropyl ether is treated with HI are tert-butyl bromide and 2-propanol.
The mechanism by which they are formed is given below.
d)
Interpretation:
The products formed and the mechanism by which they are formed when ethyl 1-methylcyclohexyl ether is treated with HI 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 1-methylcyclohexyl ether is treated with HI.
Answer to Problem 24MP
The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.
The mechanism by which they are formed is given below.
Explanation of Solution
The reaction occurs following SN1 mechanism. The acid protonates the ether initially and the protonated ether eliminates ethanol to produce a stable tert-butyl carbocation. In the next step the iodide ion attacks the carbocation to yield tert-butyl iodide.
The products formed when ethyl 1-methylcyclohexyl ether is treated with HI are 1-iodo-1-methylcyclohexane and ethanol.
The mechanism by which they are formed is given below.
All the reactions (a), (b), (c) and (d) occur through SN1 mechanism.
All the reactions, (a), (b), (c) and (d) take place following SN1 mechanism. The protonated
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Chapter 18 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
- Determine whether the following reaction is an example of a nucleophilic substitution reaction: Br OH HO 2 -- Molecule A Molecule B + Br 义 ollo 18 Is this a nucleophilic substitution reaction? If this is a nucleophilic substitution reaction, answer the remaining questions in this table. Which of the reactants is referred to as the nucleophile in this reaction? Which of the reactants is referred to as the organic substrate in this reaction? Use a ŏ + symbol to label the electrophilic carbon that is attacked during the substitution. Highlight the leaving group on the appropriate reactant. ◇ Yes O No O Molecule A Molecule B Molecule A Molecule B टेarrow_forwardPlease correct answer and don't used hand raitingarrow_forwardPlease correct answer and don't used hand raitingarrow_forward
- Pheromone G of the maize stalk borer, chilo partelus, can be synthesized based on the partial scheme shown below. Complete the scheme by identifying the structures of the intermediate compounds A, B, C, D, E, F and pheromone G. Indicate stereochemistry where relevantarrow_forwardQ8: Draw the resonance structures for the following molecule. Show the curved arrows (how you derive each resonance structure). Circle the major resonance contributor. одarrow_forwardQ9: Explain why compound I is protonated on O while compound II is protonated on N. NH2 DD I II NH2arrow_forward
- Complete the following reaction by identifying the principle organic product of the reactionarrow_forwardDenote the dipole for the indicated bonds in the following molecules. ✓ H3C CH3 B F-CCl3 Br-Cl H3C —Si(CH3)3 CH3 OH HO HO H HO OH vitamin Carrow_forward(a) What is the hybridization of the carbon in the methyl cation (CH3*) and in the methyl anion (CH3)? (b) What is the approximate H-C-H bond angle in the methyl cation and in the methyl anion?arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning