A student wanted to know whether the greater proximity of the ucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl.Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?

A student wanted to know whether the greater proximity of the ucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl.Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter26: Aldol And Claisen Reactions

Section: Chapter Questions

Problem 44E

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A student wanted to know whether the greater proximity of the nucleophile to the C-2 carbon in the transition state is what causes the 1,2-addition product to be formed faster when 1,3-butadiene reacts with HCl. Therefore, she decided to investigate the reaction of 2-methyl-1,3-cyclohexadiene with HCl. Her friend told her that she should use 1-methyl-1,3-cyclohexadiene instead. Should she follow her friend’s advice?
Explain why 1-bromo-2,2-dimethylpropane has difficulty undergoing both SN2 and SN1 reactions. . Can it undergo E2 and E1 reactions?
Why is the alkyl bromide substrate below not capable of undergoing an E2 elimination reaction upon treatment with potassium hydroxide (KOH) in ethanol (EtOH)? -Br– is too poor a leaving group. -Too much angle strain would be present in the alkene product. -Potassium hydroxide is a poor base to use in E2 reactions. -An anti-periplanar E2 elimination cannot occur due to the lack of a beta-hydrogen in the substrate
which will proceed more easily at room temperature the bromination of cyclohexene or the bromination of benzene?
Enolates are formed by deprotonation of an α-carbon hydrogen. Answer the following questions about enolate formation. In the molecule shown, select the α-carbon hydrogen that would be removed to form an enolate when NaOEt is used as a base. Draw the thermodynamic enolate that results for the molecule in Part 1. Draw only the enolate resonance form that includes a formal charge on the α carbon. Be sure to indicate that formal charge as well as any lone pair of electrons in your answer.
Draw the molecule: Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other.Show what products might be expected from the reaction of 2-bromo-3-methylbutane (a moderately hindered 2∘∘ alkyl halide) with sodium ethoxide. Do not worry about sterechemistry inther SN2 product for this problem. Don't forget about stereochemistry.
Why does increasing alkyl substitution increase the rate of an E2 reaction?
Under second-order conditions (strong base/nucleophile), SN2 and E2 reactions may occur simultaneously and compete with each other. Show what products might be expected from the reaction of 2-bromo-3-methyl butane (a moderately hindered 2∘ alkyl halide) with sodium ethoxide. Do not worry about stereochemistry in the SN2 product for this problem. Don't forget about stereochemistry.
Explain using resonance structures of the intermediates (please explain and draw them out) why the bromination of phenol is faster than the bromination of phenyl ester?
Which solvent would make the bromination through electrophilic aromatic substitution faster? Pentane Toluene Propanoic acid Petroleum ether
1. Which of the following is the strongest nucleophile? Refer to the diagram below with an MeOH, MeSH, etc. 2. Which of the following is true about the stereochemistry of SN1 reaction?a.retention of configuration at the electrophilic centerb.50:50 mixture of retention and inversion of configuration at the electrophilic centerc.inversion of configuration at the electrophilic centerd. slightly more inversion than retention at the electrophilic center
Can you explain about the order of reactivity in an E1 elimination? And for these compounds, how to list them in increasing reactivity? 1. CH2CH3CHBrCH3 2. CH3CH2CH2CH2Br 3. (CH3)3CBr