give answer in 2 step with explanation at the end of each step and final answer at the end:Week 9 - Introduction to Multi-Step Synthesis
EE ——————————— Another C-C bond forming reaction tht you hav lesmed sth mcleophilc pening of sn
epoxide
3. (551) Propose dstep synthesis 0 prepare compound using an eporidtion
Short Sythe Projects reaction ud mcleophilc addition oa epovide
One major goal of organic chemistry is 0 crate new molecules. You have been cain the
individual reaction. Now ry to put her together to make bigger molecules.
1. (5 is) Propose a fective synthesis of an ther from a is-carbon acobol snd a
branched alkyl halide wing the Willamaon ether ymibess. Include depeoionations
steps. Consider the effect of sei hindrance
Alph-alkylaion reactions ae incredibly important C-C bond forming escions.
4 (5 ts cach) Propose plan 0 synthesize compound staring with ey.
cyclohexanone. oclule an alpha-akarion, reduction reaction wd sn
erifcation ecction.
Reactions involving Carbon Nucleophiles and Carbon Electrophiles ar important because these
reactions form new CC bods thus complex carbon skeleton cen be assembled
One C-C bond forming reaction that you have eamed ca be used 1 8d alkyl groups 1 an
aye
2 (5 pus) Provide a synthetic route fr converting etbyne nto 8 10-15 carbon long
product that contains an internal alkyne. Incl deprotonation scp.
Question:
give answer in 2 step with explanation at the end of each step and final answer at the end:Week 9 - Introduction to Multi-Step Synthesis
EE ——————————— Another C-C bond forming reaction tht you hav lesmed sth mcleophilc pening of sn
epoxide
3. (551) Propose dstep synthesis 0 prepare compound using an eporidtion
Short Sythe Projects reaction ud mcleophilc addition oa epovide
One major goal of organic chemistry is 0 crate new molecules. You have been cain the
individual reaction. Now ry to put her together to make bigger molecules.
1. (5 is) Propose a fective synthesis of an ther from a is-carbon acobol snd a
branched alkyl halide wing the Willamaon ether ymibess. Include depeoionations
steps. Consider the effect of sei hindrance
Alph-alkylaion reactions ae incredibly important C-C bond forming escions.
4 (5 ts cach) Propose plan 0 synthesize compound staring with ey.
cyclohexanone. oclule an alpha-akarion, reduction reaction wd sn
erifcation ecction.
Reactions involving Carbon Nucleophiles and Carbon Electrophiles ar important because these
reactions form new CC bods thus complex carbon skeleton cen be assembled
One C-C bond forming reaction that you have eamed ca be used 1 8d alkyl groups 1 an
aye
2 (5 pus) Provide a synthetic route fr converting etbyne nto 8 10-15 carbon long
product that contains an internal alkyne. Incl deprotonation scp.
This is AI generated Response.
Asked by: Rahul
Created at: 2025-11-20 17:26:26
Final Answer:
RenderedRaw Text
Did you like this answer?
Certainly! I’ll answer question 1 as requested, in **2 steps**, with explanations after each step, and the final answer at the end.
---
## Question 1
**Propose an effective synthesis of an ether from a six-carbon alcohol and a branched alkyl halide using the Williamson ether synthesis. Include deprotonation steps. Consider the effect of steric hindrance.**
---
### **Step 1: Choose the Roles for Each Reactant**
- **Six-carbon alcohol:** 1-hexanol (CH₃(CH₂)₅OH)
- **Branched alkyl halide:** tert-butyl bromide (t-BuBr, (CH₃)₃CBr)
**Steric Hindrance Consideration:**
- The Williamson ether synthesis works best when the alkyl halide is **primary** (less hindered) and the alkoxide is more nucleophilic and less hindered.
- If the **alkyl halide is branched (like t-BuBr, tertiary)**, an E2 elimination occurs instead of substitution.
- So, use **1-hexanol as the alkoxide (nucleophile)** and **t-BuBr as the alkyl halide (electrophile)** is **NOT ideal**.
- **Reverse roles:** Use branched alcohol to make the alkoxide, and use primary alkyl halide as electrophile.
**Explanation:**
Steric hindrance around the halide carbon (as in t-BuBr) makes SN2 substitution (needed for Williamson synthesis) very slow or impossible. Instead, use the less hindered compound (1-bromohexane) as the alkyl halide.
---
### **Step 2: Synthesis Steps with Deprotonation**
1. **Deprotonation:**
- Treat the six-carbon alcohol (1-hexanol) with a strong base (e.g., NaH or Na metal) to deprotonate and form the hexoxide ion:
\[
\text{CH}_3(\text{CH}_2)_5\text{OH} + \text{NaH} \rightarrow \text{CH}_3(\text{CH}_2)_5\text{O}^- \text{Na}^+ + \text{H}_2
\]
2. **SN2 Reaction with Branched Alkyl Halide:**
- React the hexoxide ion with a **less hindered** branched alkyl halide, such as 2-bromopropane (isopropyl bromide):
\[
\text{CH}_3(\text{CH}_2)_5\text{O}^- \text{Na}^+ + (\text{CH}_3)_2\text{CHBr} \rightarrow \text{CH}_3(\text{CH}_2)_5\text{OCH(CH}_3)_2 + \text{NaBr}
\]
**Explanation:**
A strong base deprotonates the alcohol to form the alkoxide, which then attacks the less sterically hindered, preferably primary or secondary, alkyl halide via SN2. Tertiary halides are avoided due to steric hindrance.
---
## **Final Answer:**
**1. Deprotonate 1-hexanol with NaH to form sodium hexoxide.**
**2. React sodium hexoxide with isopropyl bromide (or another branched but not tertiary alkyl halide) to form the ether via the Williamson synthesis.**
**Product:**
**Hexyl isopropyl ether**
\[
\text{CH}_3(\text{CH}_2)_5\text{OCH(CH}_3)_2
\]
**Note:** Avoid using tertiary alkyl halides in the Williamson synthesis due to steric hindrance.
VIPSolutions focuses on clear, step‑by‑step explanations so you can learn quickly. Whether you need an AI‑generated walkthrough or a short hint to get unstuck, each solution is organized for fast reading and easy review later.
Search similar questions, compare approaches, and bookmark the best answers for revision. Our goal is simple: quick, reliable study help that feels natural—not noisy.
VIPSolutions
Week 9 - Introduction to Multi-Step Synthesis
EE ——————————— Another C-C bond forming reaction tht you hav lesmed sth mcleophilc pening of sn
epoxide
3. (551) Propose dstep synthesis 0 prepare compound using an eporidtion
Short Sythe Projects reaction ud mcleophilc addition oa epovide
One major goal of organic chemistry is 0 crate new molecules. You have been cain the
individual reaction. Now ry to put her together to make bigger molecules.
1. (5 is) Propose a fective synthesis of an ther from a is-carbon acobol snd a
branched alkyl halide wing the Willamaon ether ymibess. Include depeoionations
steps. Consider the effect of sei hindrance
Alph-alkylaion reactions ae incredibly important C-C bond forming escions.
4 (5 ts cach) Propose plan 0 synthesize compound staring with ey.
cyclohexanone. oclule an alpha-akarion, reduction reaction wd sn
erifcation ecction.
Reactions involving Carbon Nucleophiles and Carbon Electrophiles ar important because these
reactions form new CC bods thus complex carbon skeleton cen be assembled
One C-C bond forming reaction that you have eamed ca be used 1 8d alkyl groups 1 an
aye
2 (5 pus) Provide a synthetic route fr converting etbyne nto 8 10-15 carbon long
product that contains an internal alkyne. Incl deprotonation scp.