Ⓡ (b) (c) 0 HO A H H₂PO4 heat KOCH₂CH₂ CH₂CH₂OH KHSO4 KOCICH.)). D H₂PO4

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34. Each of the following alcohols or alkyl halides has been subjected to either acid-catalyzed dehydration or base dehydrohalogenation respectively and yields a mixture of two or more isomeric alkenes. Identify the  alkenes in each case, and predict which one is the major product on the basis of either Zaitsev rule, stability of the alkene or rearrangement.  Give the IUPAC name, including stereochemistry where necessary, of each organic reactant and product and state whether it is the E1 or E2 product

**Chemical Reaction Schemes**

(a) **Structure:**
- A linear alkane chain with an alcohol group (OH) attached to the second carbon.

**Reaction Conditions:**
- Reactant: \( \text{H}_3\text{PO}_4 \) (Phosphoric acid)
- Condition: Heat

(b) **Structure:**
- A cyclopentane ring with a chlorine atom (Cl) and a side chain consisting of a three-carbon alkane branch.

**Reaction Conditions:**
- Reactant: KOCH\(_2\)CH\(_3\) (Potassium ethoxide)
- Solvent: CH\(_3\)CH\(_2\)OH (Ethanol)

(c) **Structure:**
- A cycloheptane ring with an ethyl group and a chlorine atom (Cl) attached.

**Reaction Conditions:**
- Reactant: KHSO\(_4\) (Potassium hydrogen sulfate)
- Condition: Heat

(d) **Structure:**
- A cyclohexane ring with a chlorine atom (Cl) and a wedge bond representing a substituent above the plane of the ring.

**Reaction Conditions:**
- Reactant: KOC(CH\(_3\))\(_3\) (Potassium tert-butoxide)
- Solvent: \( \text{t-BuOH} \)

(e) **Structure:**
- A bicyclic structure with two bridgehead carbon atoms and a chlorine atom (Cl) attached to one of the bridgehead positions.

**Reaction Conditions:**
- Reactant: H\(_3\)PO\(_4\) (Phosphoric acid)
- Condition: Heat

This sequence illustrates various organic chemical reactions involving cyclic structures subjected to different reagents and conditions. The reactions typically involve substitution or elimination processes influenced by the type of reagent and heating applied.
Transcribed Image Text:**Chemical Reaction Schemes** (a) **Structure:** - A linear alkane chain with an alcohol group (OH) attached to the second carbon. **Reaction Conditions:** - Reactant: \( \text{H}_3\text{PO}_4 \) (Phosphoric acid) - Condition: Heat (b) **Structure:** - A cyclopentane ring with a chlorine atom (Cl) and a side chain consisting of a three-carbon alkane branch. **Reaction Conditions:** - Reactant: KOCH\(_2\)CH\(_3\) (Potassium ethoxide) - Solvent: CH\(_3\)CH\(_2\)OH (Ethanol) (c) **Structure:** - A cycloheptane ring with an ethyl group and a chlorine atom (Cl) attached. **Reaction Conditions:** - Reactant: KHSO\(_4\) (Potassium hydrogen sulfate) - Condition: Heat (d) **Structure:** - A cyclohexane ring with a chlorine atom (Cl) and a wedge bond representing a substituent above the plane of the ring. **Reaction Conditions:** - Reactant: KOC(CH\(_3\))\(_3\) (Potassium tert-butoxide) - Solvent: \( \text{t-BuOH} \) (e) **Structure:** - A bicyclic structure with two bridgehead carbon atoms and a chlorine atom (Cl) attached to one of the bridgehead positions. **Reaction Conditions:** - Reactant: H\(_3\)PO\(_4\) (Phosphoric acid) - Condition: Heat This sequence illustrates various organic chemical reactions involving cyclic structures subjected to different reagents and conditions. The reactions typically involve substitution or elimination processes influenced by the type of reagent and heating applied.
The image presents a series of chemical reactions with molecular structures, focusing on synthesis pathways. Below is a detailed transcription and brief explanation of each step involved.

### Reaction (e):
- **Starting Material:** A six-carbon chain with a bromine atom on the third carbon.
- **Reagents:** 
  - NaOCH₂CH₃ (sodium ethoxide)
  - CH₃CH₂OH (ethanol)
- **Description:** This reaction involves a nucleophilic substitution where the bromine atom is likely replaced by an ethoxy group.

### Reaction (f):
- **Starting Material:** Cyclohexanol.
- **Reagents and Conditions:** 
  - KHSO₄ (potassium bisulfate)
  - Heat
- **Description:** This is likely an elimination reaction, where the hydroxyl group is removed, forming a cyclohexene via dehydration.

### Reaction (g):
- **Starting Material:** A bridged bicyclic compound with a chlorine substituent.
- **Reagents:** 
  - KOCH₂CH₃ (potassium ethoxide)
  - CH₃CH₂OH (ethanol)
- **Description:** The reaction probably involves substitution where the chlorine atom is replaced by an ethoxy group.

### Reaction (h):
- **Starting Material:** A six-carbon chain with a fluorine atom on the second carbon.
- **Reagents:**
  - KOCH(CH₃)₂ (potassium isopropoxide)
  - (CH₃)₂CHOH (isopropanol)
- **Description:** This reaction involves nucleophilic substitution or elimination, possibly forming a new bond with the provided conditions.

Each reaction showcases typical organic transformations such as nucleophilic substitution and elimination, relevant to synthetic organic chemistry.
Transcribed Image Text:The image presents a series of chemical reactions with molecular structures, focusing on synthesis pathways. Below is a detailed transcription and brief explanation of each step involved. ### Reaction (e): - **Starting Material:** A six-carbon chain with a bromine atom on the third carbon. - **Reagents:** - NaOCH₂CH₃ (sodium ethoxide) - CH₃CH₂OH (ethanol) - **Description:** This reaction involves a nucleophilic substitution where the bromine atom is likely replaced by an ethoxy group. ### Reaction (f): - **Starting Material:** Cyclohexanol. - **Reagents and Conditions:** - KHSO₄ (potassium bisulfate) - Heat - **Description:** This is likely an elimination reaction, where the hydroxyl group is removed, forming a cyclohexene via dehydration. ### Reaction (g): - **Starting Material:** A bridged bicyclic compound with a chlorine substituent. - **Reagents:** - KOCH₂CH₃ (potassium ethoxide) - CH₃CH₂OH (ethanol) - **Description:** The reaction probably involves substitution where the chlorine atom is replaced by an ethoxy group. ### Reaction (h): - **Starting Material:** A six-carbon chain with a fluorine atom on the second carbon. - **Reagents:** - KOCH(CH₃)₂ (potassium isopropoxide) - (CH₃)₂CHOH (isopropanol) - **Description:** This reaction involves nucleophilic substitution or elimination, possibly forming a new bond with the provided conditions. Each reaction showcases typical organic transformations such as nucleophilic substitution and elimination, relevant to synthetic organic chemistry.
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