Indicate how you would synthesize each of the following substances from the given organic starting materials and other necessary organic or inorganic reagents. Specify reagents and conditions. (b) \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{Br}\) from \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO}\) from \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) from ethylene

Short Answer

Expert verified
(b) To synthesize \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{Br}\) from \(\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH\), first react with H2SO4 to form \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2}\), then use NBS in the presence of light to add the bromine, forming the desired compound. (c) To synthesize \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO}\) from \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\), first oxidize using PCC to form \(\mathrm{CH}_{3}\mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\mathrm{C}=O\), then react with CH3MgBr to form the final product. (d) To synthesize \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) from ethylene, first perform epoxidation using m-CPBA, then react with NaOMe in methanol to open the epoxide ring and form the desired compound.

Step by step solution

01

Convert alcohol to alkene

For this conversion, use sulfuric acid (H2SO4) as the reagent. The reaction will undergo dehydration, forming the alkene. \[ \left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH} \xrightarrow[\text{H2SO4}]{\text{Heat}} \left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \]
02

Add halogen to the alkene

To add a halogen, use N-Bromosuccinimide (NBS) in the presence of light. This will form an allylic bromide by a radical reaction. \[ \left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \xrightarrow[\text{NBS}]{\text{Light}} \left(\mathrm{CH}_{3}\right)_{2} \mathrm{CH}-\mathrm{CH}_{2} \mathrm{Br} \] (c) Synthesis of \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO}\) from \(\left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3}\):
03

Convert alcohol to ketone

To make this conversion, use PCC (Pyridinium Chlorochromate) as the oxidizing agent. The secondary alcohol will be oxidized to a ketone. \[ \left(\mathrm{CH}_{3}\right)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{CH}_{3} \xrightarrow[\text{PCC}]{\text{CH2Cl2}} \mathrm{CH}_{3}\mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\mathrm{C}=O \]
04

Grignard Reaction to Form Aldehyde

Prepare a Grignard Reagent, Methylmagnesium bromide (CH3MgBr), and use Diethyl ether (Et2O) as a solvent. Then, react with ethanal to form the desired product. \[ \mathrm{CH}_{3}\mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2}\mathrm{C}=O + \mathrm{CH}_{3}\mathrm{MgBr} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{C}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHO} \] (d) Synthesis of \(\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3}\) from ethylene:
05

Epoxidation of ethylene

To transform ethylene into an epoxide, use a peroxy acid, such as meta-chloroperoxybenzoic acid (m-CPBA) as a reagent. \[ \mathrm{CH}_{2}=\mathrm{CH}_{2} \xrightarrow[\text{m-CPBA}]{} \mathrm{CH}_{2}\mathrm{OCH}_{2} \]
06

Nucleophilic ring-opening of epoxide

To open the epoxide ring, use Sodium Methoxide (NaOMe). The nucleophile will attack the epoxy carbon and form the new C-O bond. \[ \mathrm{CH}_{2}\mathrm{OCH}_{2} \xrightarrow[\text{NaOMe}]{\text{MeOH}} \mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{CH}_{2} \mathrm{OCH}_{3} \]

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