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Starting with propane, how would you form the following target compound? Place the reagents in the proper order. You may use a reagent more than once.

Possible reagents:
A. [tex]\[ \xrightarrow{Cl_2, h\nu} \][/tex]
B. [tex]\[ \xrightarrow[\text{2)} CH_3 OTs]{\text{1)} NaH} \][/tex]
C. LDA (xs)
D. [tex]\[ \xrightarrow[\text{Lindlar}]{H_2} \][/tex]
E. [tex]\[ \xrightarrow[\text{DCM}]{Br_2} \][/tex]
F. [tex]\[ \xrightarrow[\text{2)} H_2O]{\text{1)} NaO} \][/tex]
G. [tex]\[ \xrightarrow[\text{Pd-C}]{H_2} \][/tex]



Answer :

GinnyAnswer
To form the target compound starting from propane, follow the detailed step-by-step sequence of reagents:

1. Starting Material: Propane (C₃H₈)

2. Step 1: Bromination
- Use reagent: [tex]\( \xrightarrow[\text{DCM}]{\text{Br}_2} \)[/tex]
- This step introduces a bromine atom through the halogenation process.
- Intermediate: 2-Bromopropane (C₃H₇Br)

3. Step 2: Alkylation
- Use reagent: [tex]\( \xrightarrow[\text{2) } \text{CH}_3\text{OTs }]{\text{1) NaH }}\)[/tex]
- Sodium hydride (NaH) deprotonates a molecule to form a nucleophile, which then attacks the tosylate ([tex]\(\text{CH}_3\text{OTs}\)[/tex]).
- Intermediate: Formation of tert-Butyl group attachment.

4. Step 3: Further Substitution to form Alcohol groups
- Use reagent: [tex]\( \xrightarrow[\text{2) } \text{H}_2\text{O }]{\text{1) NaO }}\)[/tex]
- Sodium oxide (NaO) followed by water addition introduces hydroxyl groups through substitution.

5. Final Structure:
- You will achieve the target compound with tert-Butyl groups and hydroxyl groups correctly placed.

Summary of Reagents:
- 1) [tex]\( \xrightarrow[\text{DCM}]{\text{Br}_2} \)[/tex]
- 2) [tex]\( \xrightarrow[\text{2) } \text{CH}_3\text{OTs }]{\text{1) NaH }}\)[/tex]
- 3) [tex]\( \xrightarrow[\text{2) } \text{H}_2\text{O }]{\text{1) NaO }}\)[/tex]

Following these steps and reagents in sequence leads from propane to the target compound with the mixed tert-Butyl and hydroxyl functionalities.

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