Devise the most efficient synthesis for the carboxylic acid below using a starting material and reagents from the tables. Give your route by specifying the number of the starting material followed by the letters of the reagents you would use beginning with the first step. The answer 4fh means treat t-butanol(4) with conc. HCl(f) then treat the product with KOH in alcohol(h). HO. Starting materials Br ton OH H3C OH Br 7 Reagents a Mg / dry ether e Ethanol, H2SO4(trace) at reflux i OsO4 b 1. CO, 2. acidic workup f Conc, HCI į Naz Cro4 / aqueous H2SO, c NACN / THF or DMF g HBr к 1. Вн,THF 2. Н,ОJaq, NaOH d NaCN / dil. aqueous H2SO4 h KOH / alcohol

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**Synthesis of Carboxylic Acid**

Objective: Devise the most efficient synthesis for the carboxylic acid shown below using a starting material and reagents from the tables provided.

### Target Carboxylic Acid:
The structure shown is a carboxylic acid with a long alkyl chain.

### Starting Materials:
1. Benzyl bromide (with benzene ring)
2. p-bromotoluene
3. 1-bromopentane
4. t-butanol
5. Hexanal
6. 2-methyl-2-propanol
7. 4-bromo-1-butanol
8. 1-octene

### Reagents:
- **a**: Mg / dry ether
- **b**: 1. CO₂  2. acidic workup
- **c**: NaCN / THF or DMF
- **d**: NaCN / dil. aqueous H₂SO₄
- **e**: Ethanol, H₂SO₄(trace) at reflux
- **f**: Conc. HCl
- **g**: HBr
- **h**: KOH / alcohol
- **i**: OsO₄
- **j**: Na₂CrO₄ / aqueous H₂SO₄
- **k**: 1. BH₃/THF  2. H₂O₂/aq. NaOH
- **l**: Epoxide

### Instruction:
To specify your synthesis route, select the number of the starting material followed by the letters corresponding to the reagents. Begin with the first step.

Example Pathway:
- The answer 4fh means treat t-butanol (4) with conc. HCl (f), then treat the product with KOH in alcohol (h).

Make sure to carefully choose the right combination of starting materials and reagents to achieve the desired carboxylic acid efficiently. Consider factors like reactivity, selectivity, and ease of purification.
Transcribed Image Text:**Synthesis of Carboxylic Acid** Objective: Devise the most efficient synthesis for the carboxylic acid shown below using a starting material and reagents from the tables provided. ### Target Carboxylic Acid: The structure shown is a carboxylic acid with a long alkyl chain. ### Starting Materials: 1. Benzyl bromide (with benzene ring) 2. p-bromotoluene 3. 1-bromopentane 4. t-butanol 5. Hexanal 6. 2-methyl-2-propanol 7. 4-bromo-1-butanol 8. 1-octene ### Reagents: - **a**: Mg / dry ether - **b**: 1. CO₂ 2. acidic workup - **c**: NaCN / THF or DMF - **d**: NaCN / dil. aqueous H₂SO₄ - **e**: Ethanol, H₂SO₄(trace) at reflux - **f**: Conc. HCl - **g**: HBr - **h**: KOH / alcohol - **i**: OsO₄ - **j**: Na₂CrO₄ / aqueous H₂SO₄ - **k**: 1. BH₃/THF 2. H₂O₂/aq. NaOH - **l**: Epoxide ### Instruction: To specify your synthesis route, select the number of the starting material followed by the letters corresponding to the reagents. Begin with the first step. Example Pathway: - The answer 4fh means treat t-butanol (4) with conc. HCl (f), then treat the product with KOH in alcohol (h). Make sure to carefully choose the right combination of starting materials and reagents to achieve the desired carboxylic acid efficiently. Consider factors like reactivity, selectivity, and ease of purification.
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