(a) (c) (d) CH3 CH2 Br CI H CH3 + CH₂ CH₂. CH3 DBN "bulky base" Br CH CH3 CH₂CH3 CH3 + CH3OH O + NaSH + Na OCH3 25°C SN1 El SN2 E2 SN1 SN2 El E2 SN1 SN2 E1 SN1 E1 E2 SN2 E2

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Chapter1: Chemical Foundations
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For each of the following reactions, circle the mechanism(s) you would expect to see and provide the major product(s). Write NR for no reaction, if you don’t expect any reaction.

The image presents a series of chemical reactions, illustrating mechanisms and reaction pathways involving nucleophilic substitutions (S_N1 and S_N2) and elimination reactions (E1 and E2).

**Diagram (a):**
- Reactants: A cyclohexyl chloride compound with a bulky base, DBN (1,5-diazabicyclo[4.3.0]non-5-ene).
- Products: Not explicitly shown, but the boxed mechanisms to the right indicate the possible pathways: S_N1, S_N2, E1, or E2.

**Diagram (b):**
- Reactants: A linear alkyl iodide compound with sodium hydrogen sulfide (NaSH).
- Products: Not explicitly shown, but the boxed mechanisms suggest pathways via S_N1, S_N2, E1, or E2.

**Diagram (c):**
- Reactants: A cycloalkyl bromide with sodium methoxide (Na^+ OCH_3^-).
- Products: Similar to the others, potential reaction pathways include S_N1, S_N2, E1, or E2 as indicated in the box.

**Diagram (d):**
- Reactants: An alkyl bromide with methanol (CH_3OH) at 25°C.
- Products: Again, potential mechanisms include S_N1, S_N2, E1, or E2 as shown in the box.

Each reaction scheme displays the reactants followed by an arrow leading to a box. Each box categorizes the potential reaction pathways, demonstrating the flexibility in organic mechanisms and the influence of factors like the nature of the base, leaving groups, and reaction conditions.
Transcribed Image Text:The image presents a series of chemical reactions, illustrating mechanisms and reaction pathways involving nucleophilic substitutions (S_N1 and S_N2) and elimination reactions (E1 and E2). **Diagram (a):** - Reactants: A cyclohexyl chloride compound with a bulky base, DBN (1,5-diazabicyclo[4.3.0]non-5-ene). - Products: Not explicitly shown, but the boxed mechanisms to the right indicate the possible pathways: S_N1, S_N2, E1, or E2. **Diagram (b):** - Reactants: A linear alkyl iodide compound with sodium hydrogen sulfide (NaSH). - Products: Not explicitly shown, but the boxed mechanisms suggest pathways via S_N1, S_N2, E1, or E2. **Diagram (c):** - Reactants: A cycloalkyl bromide with sodium methoxide (Na^+ OCH_3^-). - Products: Similar to the others, potential reaction pathways include S_N1, S_N2, E1, or E2 as indicated in the box. **Diagram (d):** - Reactants: An alkyl bromide with methanol (CH_3OH) at 25°C. - Products: Again, potential mechanisms include S_N1, S_N2, E1, or E2 as shown in the box. Each reaction scheme displays the reactants followed by an arrow leading to a box. Each box categorizes the potential reaction pathways, demonstrating the flexibility in organic mechanisms and the influence of factors like the nature of the base, leaving groups, and reaction conditions.
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