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
Want to see more full solutions like this?
Chapter 18 Solutions
Organic Chemistry - With Access (Custom)
- Experiment 27 hates & Mechanisms of Reations Method I visual Clock Reaction A. Concentration effects on reaction Rates Iodine Run [I] mol/L [S₂082] | Time mo/L (SCC) 0.04 54.7 Log 1/ Time Temp Log [ ] 13,20] (time) / [I] 199 20.06 23.0 30.04 0.04 0.04 80.0 22.8 45 40.02 0.04 79.0 21.6 50.08 0.03 51.0 22.4 60-080-02 95.0 23.4 7 0.08 0-01 1970 23.4 8 0.08 0.04 16.1 22.6arrow_forward(15 pts) Consider the molecule B2H6. Generate a molecular orbital diagram but this time using a different approach that draws on your knowledge and ability to put concepts together. First use VSEPR or some other method to make sure you know the ground state structure of the molecule. Next, generate an MO diagram for BH2. Sketch the highest occupied and lowest unoccupied MOs of the BH2 fragment. These are called frontier orbitals. Now use these frontier orbitals as your basis set for producing LGO's for B2H6. Since the BH2 frontier orbitals become the LGOS, you will have to think about what is in the middle of the molecule and treat its basis as well. Do you arrive at the same qualitative MO diagram as is discussed in the book? Sketch the new highest occupied and lowest unoccupied MOs for the molecule (B2H6).arrow_forwardQ8: Propose an efficient synthesis of cyclopentene from cyclopentane.arrow_forward
- Q7: Use compound A-D, design two different ways to synthesize E. Which way is preferred? Please explain. CH3I ONa NaOCH 3 A B C D E OCH3arrow_forwardPredict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forward(10 pts) The density of metallic copper is 8.92 g cm³. The structure of this metal is cubic close-packed. What is the atomic radius of copper in copper metal?arrow_forward
- Predict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forwardPredict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2).arrow_forwardQ3: Rank the following compounds in increasing reactivity of E1 and E2 eliminations, respectively. Br ca. go do A CI CI B C CI Darrow_forward
- Q5: Predict major product(s) for the following reactions. Note the mechanism(s) of the reactions (SN1, E1, SN2 or E2). H₂O דיי "Br KN3 CH3CH2OH NaNH2 NH3 Page 3 of 6 Chem 0310 Organic Chemistry 1 HW Problem Sets CI Br excess NaOCH 3 CH3OH Br KOC(CH3)3 DuckDuckGarrow_forwardQ4: Circle the substrate that gives a single alkene product in a E2 elimination. CI CI Br Brarrow_forwardPlease calculate the chemical shift of each protonsarrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT