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Ch. 17 - Reactions of Aromatic Compounds
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh. 17 - Reactions of Aromatic CompoundsProblem 39a
Chapter 17, Problem 39a

Show how you would synthesize the following compounds, using the indicated starting materials.
(a) 3-phenylbutan-1-ol from styrene

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Step 1: Begin by understanding the target compound, 3-phenylbutan-1-ol. It contains a phenyl group attached to a butanol chain with the hydroxyl group (-OH) at the terminal position. The starting material, styrene, is an aromatic compound with a vinyl group (-CH=CH2) attached to the benzene ring.
Step 2: Perform a hydroboration-oxidation reaction on styrene to convert the vinyl group into a primary alcohol. In the hydroboration step, use BH3·THF (borane in tetrahydrofuran) to add boron and hydrogen across the double bond in a syn addition manner. Then, oxidize the intermediate using H2O2 and NaOH to yield 2-phenylethanol.
Step 3: Extend the carbon chain of 2-phenylethanol to form 3-phenylbutan-1-ol. This can be achieved by reacting 2-phenylethanol with a Grignard reagent. First, prepare a Grignard reagent, such as ethylmagnesium bromide (CH3CH2MgBr), which will add an ethyl group to the molecule.
Step 4: React 2-phenylethanol with the Grignard reagent under appropriate conditions. The Grignard reagent will attack the carbon atom adjacent to the hydroxyl group, forming a new C-C bond and extending the chain to create 3-phenylbutan-1-ol.
Step 5: Purify the product using standard organic chemistry techniques, such as distillation or recrystallization, to isolate 3-phenylbutan-1-ol. Confirm the structure using spectroscopic methods like NMR or IR to ensure the synthesis was successful.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction in organic chemistry where a nucleophile attacks an electrophilic carbon atom, leading to the formation of a new bond. In the synthesis of 3-phenylbutan-1-ol from styrene, the nucleophile can be a hydride ion or an alcohol, which adds to the electrophilic carbon of the styrene's double bond, facilitating the formation of the desired alcohol.

Grignard Reagents

Grignard reagents are organomagnesium compounds that act as strong nucleophiles in organic synthesis. They can react with carbonyl compounds to form alcohols. In this synthesis, a Grignard reagent derived from styrene can be used to add a carbon chain to a carbonyl compound, ultimately yielding 3-phenylbutan-1-ol through subsequent hydrolysis.

Rearrangement Reactions

Rearrangement reactions involve the reorganization of atoms within a molecule to form a new structure. In the context of synthesizing 3-phenylbutan-1-ol, understanding how to manipulate the carbon skeleton through rearrangements can be crucial, especially if intermediate compounds are formed that require structural adjustments to achieve the final product.
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