Concept explainers
Interpretation:Significance of the dashed bonds in the structure of the non-classical cation should be given and the feature that makes this cation non-classical should be identified.
Concept introduction:A classical carbocation represented as
Classical carbocation prefers to be tri-coordinated and achieve stabilization via hyperconjugation. This indicates that an adjacent
A non-classical cation is a unique carbocation that involves the delocalization of electron density of filled bonding orbital over three carbons. It exists for systems such as phenonium ions,norbornyltosylates, brosylate, and nortricyclonium cations. They can be understood as carbocation that is a transition state for two asymmetric equilibrium cations.
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EBK EXPERIMENTAL ORGANIC CHEMISTRY: A M
- a. How many vinylic hydrogens does cyclopentene have? b. How many allylic hydrogens does it have?arrow_forward3. What condition(s) would you use to convert the Diels-Alder product (boxed) into each of the diastereomeric diol-imides A, B, and C below. H 30-40-50 1 HO,, HO H H A N ? HO,,. HO C (racemic) ? но. HO H H Barrow_forward4. Isit possible for the diene shown below to undergo a Diels-Alder reaction with maleic anhydride? Explain.arrow_forward
- 2) a. 2,3-Di-tert-butyl-1,3-butadiene does not under go Diels-Alder reactions. Explain. b. How can you account for the fact that (Z)-1,3-pentadiene is much less reactive than (E)-1,3- pentadiene in Diels-Alder reaction?arrow_forward5. Why azulene is a polar compound. Explain. 6. Rank the following comounds in order of decreasing rectivity with a typical Nu. Explain Chlorobenzene, 2-chloropyridine, 3-chloropyridine and 4-chloropyridinearrow_forwardHow many E-Z stereoisomers are there of the molecule shown below, including the molecule shown? This is an insight question to see who can apply their minds. Attachments OH N A. 4 B. 2 C. 32 D. 8 E. 128 F. 64 G. 16 Assign the stereochemical prefix(es) to the name of the following molecule. Attachments A. (1Z)-hepta-1,5-diene B. (1E,5E)-hepta-1,5-diene C. (5E)-hepta-1,5-diene D. (1E,5Z)-hepta-1,5-diene E. (5Z)-hepta-1,5-diene F. (1E)-hepta-1,5-diene G. (1Z,5E)-hepta-1,5-diene H. (1Z,5Z)-hepta-1,5-diene ||arrow_forward
- 1) In the Diels-Alder reaction there are two reaction components: a DIENE (must be a conjugated diene); and a DIENOPHILE (an ene usually with electron withdrawing substituents). a. Bicyclic diene A reacts readily with appropriate alkenes by the Diels-Alder reaction, whereas diene B is totally unreactive. Explain. b. Write the three reactions and show the product for diene A reacting with dienophiles I, II, and III. Rank I, II, and III in terms of their expected reactivity in a Diels Alder reaction. Justify your assigned ranks. A B || LOCH3 IIIarrow_forward2. Determine the starting material that could have been used to synthesize the follwoing Diels Alder adducts shown below. Show stereochemistry when applicable. OMe „CN LOCH3 3. Rank the reactivity of following molecule towards hydrogenation reaction. 1 being most reactive and 4 being the least reactive. Provide a brief explanation.arrow_forward] Draw the structure of Diels-Alder cycloadduct formed via an endo 3. [a, transition state structure involving the diene and dienophile shown here. [b Formulate the endo transition structure that leads to the product. [c is observed. Does it correspond to a primary or a secondary KIE? Explain. [d. the 'inverse' variety? Explain. -CO2ET ]A KIE ] Is the KIE of the 'normal' orarrow_forward
- Classify the following substituents according to whether they are electron donors or electron acceptors relative to hydrogen by the resonance and the inductive mechanisms. a = acceptor d = donor n = no effect :0: 1. -OCH₂CH3 Inductive effect Resonance effect OCH₂CH3 :::: 2. -CCH₂CH₂CCH3 3. NHCH₂CH₂CH₂C=N; Inductive effect Inductive effect Resonance effect Resonance effectarrow_forwardWhich of the following rings is the most strained? cyclopropene; cyclopropane; cyclobutane; cyclopentane; cyclohexane after finding the most strained compound explain why and compare it to the other answer choices, explaining why they do not work as an answer.arrow_forwardPlease ex plain and Please show all arrow pushing mechaarsas. Thank you!arrow_forward
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