3. Identify the dominant mechanism(s) (SN1, SN2, E1, E2) that occurs in each reaction and fill in the boxes with the missing reagent or product. (Hint: Identify the type of nucleophile/base and electrophile you're dealing with to help narrow your options.) Mechanism Starting Material Reagent Major Organic Product(s) КОСН-СН, Br LİNHCH2CH3 NANH2 H Br

3. Identify the dominant mechanism(s) (SN1, SN2, E1, E2) that occurs in each reaction and fill in the boxes with the missing reagent or product. (Hint: Identify the type of nucleophile/base and electrophile you're dealing with to help narrow your options.) Mechanism Starting Material Reagent Major Organic Product(s) КОСН-СН, Br LİNHCH2CH3 NANH2 H Br

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 20E

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Q2. For the reactions below, draw out the reactions as shown and answer the following questions for each example: (i) Identify the nucleophile/electrophile/base/leaving group where applicable (ii) Identify each mechanism as SNl, SN2, E1 or E2. (iii) Insert curly arrows to represent the reaction mechanism. с. CI NaO НО NaCI 95
Q10. For each of the following reactions (a-b), predict whether the substitution is more likely to occur following an Sn1 or Sn2 mechanism; explain your reasoning. Draw the products of each nucleophilic substitution paying particular attention to the stereochemistry of carbon 1. a) Br, CH3 MeOH H3C b) Br NaOH 1 DMF* H3C *N,N-dimethylformamide
Q2. For the reactions below, draw out the reactions as shown and answer the following questions for each example: (i) Identify the nucleophile/electrophile/base/leaving group where applicable (ii) Identify each mechanism as SŅ1, SN2, E1 or E2. (iii) Insert curly arrows to represent the reaction mechanism. а. Br Nal NaBr + H H CI- NaOH H20 NaCI + + + H H. b.
When HCI, HBr, and HI were used as HX in the next reaction, the rates of all reactions were almost the same. below Answer the question. OH HX CH3 CH3 H2O (1) Show the ions that act as each nucleophile in order from the one that is considered to have the highest nucleophilic reactivity. (2) Explain the reason why you thought that the order was (1). (3) Explain why the reaction rates were almost the same regardless of which HX was used. (4) Nax was used instead of HX, but the reaction did not proceed. Explain the reason for this.
b) 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.
Q3. For the substitution reactions below, draw out the reactions as shown and answer the following questions for each example: (i) Draw the structure of the unknown product(s) of the reaction. (ii) Identify the nucleophile, electrophile and the leaving group for each step. (iii) Identify each mechanism as Snl or SN2. (iv) Insert curly arrows to represent the reaction mechanism. а. NaOH Product A Product B
Q3. For the substitution reactions below, draw out the reactions as shown and answer the following questions for each example: (i) Draw the structure of the unknown product(s) of the reaction. (ii) Identify the nucleophile, electrophile and the leaving group for each step. (iii) Identify each mechanism as Sn1 or Sn2. (iv) Insert curly arrows to represent the reaction mechanism. b. Br NH3 Product C Product D
4. Complete the phrases with one or more of the following terms: SNI, SN2, E1, E2. a) The reaction takes place in two or more steps. b) The reaction goes through a carbocation. c) The rate determining step has two reactants. d) The rate is independent of the concentration of nucleophile or base. e) Zaitsev's rule is often applicable to the products..
Q10. For each of the following reactions (a-b), predict whether the substitution is more likely to occur following an Sn1 or Sn2 mechanism; explain your reasoning. Draw the products of each nucleophilic substitution paying particular attention to the stereochemistry of carbon 1. а) Br CH3 MeOH H3C b) Br NaOH DMF* H3C *N,N-dimethylformamide
3) Any compound or ion with at least one lone pair can be considered a base and/or a nucleophile. The relative basicity and nucleophilicity of the species is one of the most important factors that determine the mechanism of a reaction on sp³-carbon atoms. Please show an example of a) a reagent that is a strong nucleophile and a strong base, b) a reagent that is a weak nucleophile and a strong base, c) a reagent that is a strong nucleophile and a weak base, d) a reagent that is a weak nucleophile and a weak base. Which nitrogen atom in the structure below is most nucleophilic? Please explain by discussing the electron density around each nitrogen atom. Show at least three resonance structures of the compound. N.
pathway (4 EPD carbon electrophile, nucleophile, leaving group, solvent, stepwise, carbocation intermediate, racemization) to solve synthetic problems. was reading the organic chemical literature and was surprised to read that this structure reacts with good Lewis/attacker nucleophiles rapidly by the SN1 pathway. Why was Prof. Mio surprised by these data? Explain these data using your knowledge of SN1 pathways. Me. Me Me OTS
Draw the reactants and complete the mechanism by drawing in the appropriate electron-flow arrows (including stereochemistry) for the following Sy2 reaction of an alkyl bromide. Represent the nucleophile as an ion. Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the grid and connecting them with bonds, including charges where needed. Indicate the mechanism by drawing the electron-flow arrows on the molecules. Arrows should start on an atom or a bond and should end on an atom, bond, or where a new bond should be created. • View Available Hint(s) + CH N H. S CH H,C C-ÖH CI HC Br HC F [1] A