Scribd
Upload
3 views

pentanol

The document outlines the retrosynthetic analysis of 2-pentanol, focusing on consonant and dissonant disconnections. The most efficient synthetic route is identified as the reduction of 2-pentanone using NaBH₄, which offers high yield and simplicity. Alternative strategies include epoxide opening and enolate alkylation, both of which are viable but more complex.

Uploaded by

Farhan Ch
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
3 views

pentanol

The document outlines the retrosynthetic analysis of 2-pentanol, focusing on consonant and dissonant disconnections. The most efficient synthetic route is identified as the reduction of 2-pentanone using NaBH₄, which offers high yield and simplicity. Alternative strategies include epoxide opening and enolate alkylation, both of which are viable but more complex.

Uploaded by

Farhan Ch
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
You are on page 1/ 4

To address the retrosynthetic analysis of 2-pentanol, we’ll break down the problem using

consonant and dissonant retrosynthetic disconnections, analyze electronic and steric


considerations, and design the most efficient forward synthesis.

🎯 Target Molecule: 2-Pentanol


Structure: CH₃–CH(OH)–CH₂–CH₂–CH₃
Functional group: Secondary alcohol (2° alcohol)
Key features: Hydroxyl at C-2, linear five-carbon chain

🧠 Retrosynthetic Analysis
1. Consonant Disconnection (Favors Natural Polarities)

This approach respects the natural polarity: nucleophile attacks electrophile.

❖ Disconnection: C–O bond

CH₃–CH(OH)–CH₂–CH₂–CH₃ ⟶ CH₃–C⁺H–CH₂–CH₂–CH₃ + OH⁻


 Disconnection pattern:

→ Equivalently, react a suitable carbonyl compound with a nucleophile.


 Retrosynthetic equivalent:
2-pentanone + hydride (H⁻) or Grignard/organometallic reagent.
 Synthetic transformation:
Reduction of 2-pentanone
 Reaction:
 2-Pentanone + NaBH₄ or LiAlH₄ → 2-Pentanol

 Assessment:
o Electronic: Favorable; carbonyl is electrophilic.
o Sterics: Minimal hindrance at ketone.
o Yield: High.
o Stereochemistry: Racemic product (RS mixture).

✅ Viable and efficient.


2. Dissonant Disconnection (Polarity-Inverted or Umpolung)

This approach inverts the expected polarity—e.g., treating normally nucleophilic centers as
electrophiles.

❖ Disconnection: C–C bond

 Break C2–C3 bond to create fragments with reversed polarity.


 Retrosynthetic idea:
Use an umpolung strategy, such as epoxide opening or enolate alkylation.

(a) Epoxide Opening Strategy

 Retrosynthetic step:

⟶ Epoxide (CH₃–CH(O)–CH₂–CH₂) + Grignard (CH₃MgBr)


CH₃–CH(OH)–CH₂–CH₂–CH₃

 Forward reaction:
o Start from 1,2-epoxypentane
o Attack with methyl Grignard at less hindered carbon (SN2-like)
 Reaction:
 Epoxide + CH₃MgBr → 2-Pentanol

 Assessment:
o Electronic: Epoxide is electrophilic.
o Steric: May lead to regioisomer mixture.
o Control: Requires regioselectivity.
o Stereochemistry: Moderate control; inversion at attacked center.

🟡 Moderate viability; less straightforward than ketone reduction.

(b) Enolate Alkylation Strategy

 Disconnection: α-alkylation of butan-2-one.

CH₃–CH(OH)–CH₂–CH₂–CH₃ ⟶ CH₃–CO–CH₂CH₃ + CH₃–I


 Retrosynthetic step:

 Forward reaction:
o Enolate formation from 2-butanone
o Alkylation with MeI
o Followed by reduction
 Reaction:
 CH₃–CO–CH₂CH₃ + LDA → Enolate
 Enolate + CH₃I → 2-Pentanone
 2-Pentanone + NaBH₄ → 2-Pentanol

 Assessment:
o Electronic: α-position is nucleophilic.
o Steric: Primary alkyl halides react well.
o Yield: Good with careful control.
o Steps: Multi-step, but flexible.

✅ Viable with moderate complexity.

🏁 Recommended Synthetic Route (Most Efficient)


📌 Best Route: Ketone Reduction (Consonant Pathway)
Forward Synthesis:

1. Starting Material: 2-Pentanone (commercially available or easily prepared).


2. Reduction:
o Reagent: NaBH₄ in MeOH or EtOH (mild, selective for ketones).
o Alternative: LiAlH₄ in ether (more reactive, less selective).
3. Work-up: Aqueous quench, extraction.

Reaction:
CH₃–CO–CH₂–CH₂–CH₃ + NaBH₄ → CH₃–CH(OH)–CH₂–CH₂–CH₃

Advantages:

 High yield
 Simple reagents
 Mild conditions
 Minimal side-products
 Shortest linear route (1 step)

🔁 Summary of Retrosynthetic Routes


Disconnecti
Type Intermediates Viability Notes
on

Consona Simple, high-yield


C–O (ketone) 2-pentanone ✅ Excellent
nt reduction

Epoxide ring Dissonan Epoxide + 🟡 Moderate Regioselectivity


Disconnecti
Type Intermediates Viability Notes
on

t Grignard required

Dissonan Multi-step, synthetically


α-Alkylation Enolate + MeI ✅ Good
t rich

Would you like a reaction scheme or mechanism illustration for any of the pathways?

You might also like