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Chapter 16: Problem 51

Starting with cyclohexanone, show how to prepare these compounds. In addition to the given starting material, use any other organic or inorganic reagents as necessary. (a) Cyclohexanol (b) Cyclohexene (c) cis-1,2-Cyclohexanediol (d) 1-Methylcyclohexanol (e) 1-Methylcyclohexene (f) 1-Phenylcyclohexanol (g) 1-Phenylcyclohexene (h) Cyclohexene oxide (i) trans-1,2-Cyclohexanediol

Short Answer

Expert verified
Question: Convert cyclohexanone into the following products and outline the synthesis steps: (a) Cyclohexanol (b) Cyclohexene (c) cis-1,2-Cyclohexanediol (d) 1-Methylcyclohexanol (e) 1-Methylcyclohexene (f) 1-Phenylcyclohexanol (g) 1-Phenylcyclohexene (h) Cyclohexene oxide (i) trans-1,2-Cyclohexanediol.

Step by step solution

01

1. Reduction of Cyclohexanone to Cyclohexanol

To prepare cyclohexanol from cyclohexanone, perform a reduction using a reducing agent such as sodium borohydride (NaBH4). This will reduce the carbonyl group (C=O) in cyclohexanone to the alcohol group (C-OH) in cyclohexanol. Reaction: Cyclohexanone + NaBH4 -> Cyclohexanol (b) Cyclohexene
02

1. Reduction

First, prepare cyclohexanol from cyclohexanone using the reduction reaction as mentioned in (a).
03

2. Dehydration

To convert cyclohexanol to cyclohexene, perform a dehydration reaction. This involves using a strong acid, such as sulfuric acid (H2SO4), to remove a molecule of water from the cyclohexanol. The resulting product is cyclohexene. Reaction: Cyclohexanol + H2SO4 -> Cyclohexene + H2O (c) cis-1,2-Cyclohexanediol
04

1. Dihydroxylation

To prepare cis-1,2-cyclohexanediol from cyclohexanone, perform a dihydroxylation reaction with potassium permanganate (KMnO4) and potassium hydroxide (KOH) as the reagents. This adds two hydroxyl groups in the cis configuration to the double bond of an alkene resulting from reduction of cyclohexanone. Reaction: Cyclohexanone + KMnO4/KOH -> cis-1,2-Cyclohexanediol (d) 1-Methylcyclohexanol
05

1. Grignard Reaction

To prepare 1-methylcyclohexanol, perform a Grignard reaction using methyl magnesium bromide (CH3MgBr) as the Grignard reagent. This reaction will add a methyl group to the carbonyl group (C=O) of cyclohexanone, forming a new alcohol (C-OH). Reaction: Cyclohexanone + CH3MgBr -> 1-Methylcyclohexanol (e) 1-Methylcyclohexene
06

1. Grignard Reaction

First, prepare 1-methylcyclohexanol from cyclohexanone as depicted in (d).
07

2. Dehydration

To convert 1-methylcyclohexanol to 1-methylcyclohexene, perform a dehydration reaction by using a strong acid such as sulfuric acid (H2SO4). This will remove a molecule of water from the cyclohexanol, forming cyclohexene. Reaction: 1-Methylcyclohexanol + H2SO4 -> 1-Methylcyclohexene + H2O (f) 1-Phenylcyclohexanol
08

1. Grignard Reaction

To prepare 1-phenylcyclohexanol, perform a Grignard reaction using phenyl magnesium bromide (C6H5MgBr) as the Grignard reagent. This reaction will add a phenyl group to the carbonyl group (C=O) of cyclohexanone, forming a new alcohol (C-OH). Reaction: Cyclohexanone + C6H5MgBr -> 1-Phenylcyclohexanol (g) 1-Phenylcyclohexene
09

1. Grignard Reaction

First, prepare 1-phenylcyclohexanol from cyclohexanone as depicted in (f).
10

2. Dehydration

To convert 1-phenylcyclohexanol to 1-phenylcyclohexene, perform a dehydration reaction by using a strong acid such as sulfuric acid (H2SO4). This will remove a molecule of water from the cyclohexanol, forming cyclohexene. Reaction: 1-Phenylcyclohexanol + H2SO4 -> 1-Phenylcyclohexene + H2O (h) Cyclohexene oxide
11

1. Epoxidation

To prepare cyclohexene oxide, start with cyclohexene and perform an epoxidation reaction using reagents such as m-chloroperoxybenzoic acid (MCPBA). This will convert the double bond of cyclohexene into an epoxide ring. Reaction: Cyclohexene + MCPBA -> Cyclohexene oxide (i) trans-1,2-Cyclohexanediol
12

1. Epoxidation

First, prepare cyclohexene oxide from cyclohexene as depicted in (h).
13

2. Epoxide Ring-Opening

To convert cyclohexene oxide into trans-1,2-cyclohexanediol, perform a ring-opening reaction using acid-catalyzed hydrolysis. This will add water to the epoxide, opening the three-membered ring and forming an alcohol on each carbon. Reaction: Cyclohexene oxide + H2O + Acid -> trans-1,2-Cyclohexanediol

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