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Concept explainers
Interpretation:
The LUMO in
Concept Introduction:
▸ Electrophiles are electron deficient species which has positive or partially positive charge. Lewis acids are electrophiles which accept electron pair.
▸ Nucleophiles are electron rich species which has negative or partially negative charge. Lewis bases are nucleophiles which donate electron pair.
▸ Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a
▸ Nucleophilic substitution reaction is a reaction in which an electron rich nucleophile attacks the positive or partial positive charge of an atom or a group of atoms to replace a leaving group.
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▸ The
▸ The
▸ An
▸ The nucleophilic substitutions in which a nucleophile replaces a leaving group are known as
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▸ Carbocation is a molecule having a carbon atom bearing three bonds and a positive formal charge.
▸ Carbocation are generally unstable because they do not have eight electrons to satisfy the octet rule.
▸ The order of stability of carbocation is such that the tertiary carbocation is the most stable whereas the primary carbocation is the least stable, and secondary carbocation lies between primary and tertiary carbocations.
▸ If primary carbocation is obtained in product, it rearranges itself to secondary or tertiary carbocation to form more stable product.
▸ If secondary carbocation is obtained in product, it rearranges itself to tertiary carbocation to form more stable product.
▸ The stability of carbocation:
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Chapter 6 Solutions
Organic Chemistry
- 5) For the following multi-step reaction involvling a carbocation Overall Transformation CH3 CH3 H-Ci: CH3.. rearrangement, draw mechanism each -C : arrows to show how intermediate is formed and fill in the blanks for the types of elementary 丰 steps that are involved in this overall Stepwise Mechanism transformation. H. CH3, CH3 Step 3: Formation (fill in the blank) What is the driving force for Step 2 in problem #5? H-Ci: H. H-CI: CH3 CH3 Step 1: Addition (fill in the blank) Step 2: Shift (fill in the blank)arrow_forwardProvide illustration/s and in-depth explanation of the difference between the Markovnikov and Anti-Markovnikov additions of HBr to alkene (5 sentences only).arrow_forwardComplete the mechanism and draw the thermodynamic product for the reaction below. Feedback بیان می -CI: :C: See Periodic Table See Hint دarrow_forward
- 3) Show a complete mechanism and predict the product for the reaction shown below. Br₂ / H₂O Please provide perspective diagrams (wedge/dash notation), resonance forms, curved arrows, formal charges, and lone pairs as need for all species involved. With reference to the intermediate(s) involved, comment on both the regiochemistry and the stereochemistry of the process.arrow_forward2. Isomerization of alkenes can be achieved through conjugate addition of nucleophiles. Examine the reaction below and answer the questions that follow: i) ii) iv) blogg Starting Alkene Alkene Product Give the chemical structure of the Alkene Product that is formed (NB: Show and label the geometry of the Alkene Product). Explain why geometry given in i) above is preferred. What is likely to be the geometry of the Starting Alkene? Give the full mechanism through which the isomerization is likely to occur.arrow_forwardIdentify the major product of the reaction of an alkene shown below. ||| 1. Hg(OAc)2, H2O 2. NaBH4, NaOH ....... ОН || IV ОН о, ОНarrow_forward
- (d) Consider the following catalyzed and non-catalyzed pathways of a substitution reaction of bromoethane. Draw an energy diagram for each of the following reactions (label all axes and include reactants, intermediates (if any) and products). CH3CH₂Br + HO CH³CH₂OH + B (non-catalyzed) ное CH3CH₂Br + CH3CH₂OH + 1 (catalyzed) CH3CH₂ + Brarrow_forward.0. For 0.1 M equimolar reaction of CH3COOH + NH3 ----> CH3-CO-O™ + NH4+ How does the concentration of ]? [CH3COOH] compare to that of [CH3-CO-O (a) Equal (b) Greater than (c) Less than) (d) not possible determine aarrow_forwardb) Explain in detail what characteristics of the alkyl halide influence whether a mechanism will be SN1 or SN2. c) Explain in detail what characteristics of a nucleophile influence whether a reaction will be SN1 or SN2.arrow_forward
- 3. Draw the structure of the major organic product that forms in each of the following reactions Specify stereochemistry where appropriate. a) b) c) ð CH₂O Br Br 1) PhyCNa/Ether 2)CH₂l Oso (cat) (CH₂N-O2H₂O pyridine/'BuOH/H₂0 OCH, 1) DIBAL (excess) -78°C -rt/3h 2) MnO₂/ CH₂C 11/3harrow_forward4. For the following reactions, develop a transition-state structure using molecular models which would account for the observed stereoselectivity. Also, describe the type of pericyclic reactions using the proper terminology. (each Br heat A & Br b) F 0°C F heat heat d) product? =& & MeO₂C OCH3 H HO 1. CO₂Me مر CO₂Me LOCH3 heat heat MeO₂C HOarrow_forwardoctane + NOx + hv (assume hydrogen on second carbon bonded the weakest) For each mechanism, provide the photolytic cycle, a source for hydroxyl radical (if needed) AND atermination step. You may stop when you have accounted for all radicals AND all VOCs are stable (i.e., ifformaldehyde is a product of your mechanism, you do not have to oxidize that molecule to).arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningOrganic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
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