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Concept explainers
a) 2-Methyl-2-propanol
Interpretation:
A method to prepare 2-methyl-2-propanol using a Grignard reagent is to be given.
Concept introduction:
Grignard reagents react with formaldehyde to produce 10 alcohols, with other
To give:
A method to prepare 2-methyl-2-propanol using a Grignard reagent.
b) 1-Methylcyclohexanol
Interpretation:
A method to prepare 1-methylcyclohexanol using a Grignard reagent is to be given.
Concept introduction:
Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.
To give:
A method to prepare 1-methylcyclohexanol using a Grignard reagent.
c) 3-Methyl-3-pentanol
Interpretation:
A method to prepare 3-methyl-3 pentanol using a Grignard reagent is to be given.
Concept introduction:
Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.
To give:
A method to prepare 3-methyl-3-pentanol using a Grignard reagent.
d) 2-Phenyl-2-butanol
Interpretation:
A method to prepare 2-phenyl-2-butanol using a Grignard reagent is to be given.
Concept introduction:
Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product
To give:
A method to prepare 2-phenyl-2-butanol using a Grignard reagent.
e) Benzyl alcohol
Interpretation:
A method to prepare benzyl alcohol using a Grignard reagent is to be given.
Concept introduction:
Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.
To give:
A method to prepare benzyl alcohol using a Grignard reagent.
f) 4-Methyl-1-pentanol
Interpretation:
A method to prepare 4-methyl-1-pentanol using a Grignard reagent is to be given.
Concept introduction:
Grignard reagents react with formaldehyde to produce 10 alcohols, with other aldehydes to yield 20 alcohols and with ketones to give 30 alcohols as the product. Esters also when treated with two molar equivalents of Grignard reagents yield 30 alcohols.
To give:
A method to prepare 4-methyl-1-pentanol using a Grignard reagent.
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Chapter 17 Solutions
Organic Chemistry
- Phenylethanol can be oxidised to phenylethanal or phenylethanoic acid, depending on the reagents used (both the alcohol and the aldehyde are of interest for their antimicrobial properties, while the acid is used to treat type II hyperammonemia): A (a) (b) (c) CoH,CH,CHO phenylethanal B C6H5CH₂CH₂OHC₂H₂CH₂CO₂H phenylethanol Suggest reagents (shown as A and B in the scheme above) that could be used to carry out the oxidation of the alcohol to the aldehyde and the acid, respectively. C6H5CH₂- Suggest two other syntheses of phenylethanoic acid, in each case indicating the starting materials and other reagents required, but not giving details of mechanism. One of your proposed syntheses must start with a compound which only contains seven carbon atoms (the acid product contains eight carbon atoms). phenylethanoic acid Phenylethanal can be converted to a hydrate in the presence of aqueous acid, though the position of equilibrium is very far to the left: H H+/H₂O OH C6H5CH₂-C-H OH Explain why…arrow_forwardCH₂-CH₂-CH₂-C-OH butanoic acid CH₂ HO–C–CH,CHCH,—CHO 3-methylpentanoic acid Name each carboxylic acid. (a) HO CH₂ CH₂ 99 - 0 B) CHICHICIO CH, Draw a condensed structural diagram for each carboxylic acid (a) Hexanoic acid (b) 3-propyloctanoic acid Iarrow_forwardHow could you convert butanoic acid into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) 1-Bromobutane (c) 1-Butenearrow_forward
- Draw a structural formula of an alkene that undergoes acid-catalyzed hydration to give each alcohol as the major product (more than one alkene may give each alcohol as the major product). (a) 3-Hexanol (b) 1-Methylcyclobutanol (c) 2-Methyl-2-butanol (d) 2-Propanolarrow_forwardArrange these compounds in order of increasing boiling point (values in °C are -42, -24, 78, and 118). (a) CH,CH,OH (b) CH,OCH, (c) CH,CH,CH, (d) CH,COOHarrow_forwardHow could you convert butanenitrile into the following compounds? Write each step showing the reagents needed. (a) 1-Butanol (b) Butylaminearrow_forward
- Which of (a)-(d) is the correct IUPAC name of the following compound? * HO O 3-methyl-1-phenyl-1-pentanol ○ 3-methyl-5-phenyl-5-pentanol ○ 3-methyl-1-benzene-1-pentanol O 1-phenyl-1-hexanolarrow_forwardFor each pair of compounds, predict which compound has a higher boiling point. then explain why that compound has a higher boiling point. (a) isopropyl bromide and n-butyl bromide (b) isopropyl chloride and tert-butyl bromide (c) 1-bromobutane and 1-chlorobutanearrow_forwardWrite in the correct reagents for these transformations: a) cyclohexanol -→ chlorocyclohexane b) 2-butanone 2-butanol ward 2-butanol 2-butanone toluene - → benzoic acid nitrobenzene → anilinearrow_forward
- Write the chemical equation showing reactants, products and catalysts needed (if any) for thefollowing reactions. Write the IUPAC name of the product right beside the structure. a) Reaction of two phenol b) Reaction of 2-bromophenol with sodium hydroxide c) Reaction of potassium phenoxide with 2-chloropentane d) Reaction of isopropyl propyl ether with HBr e) Reaction of 3-methylpentan-3-ol with sulfuric acid f) Dehydration of 1,5-hepta-diolg) Oxidation of 1-decanolh) Hydration od hepta-2,3-dienearrow_forwardPlease answer my qyestion carfulle and fastarrow_forwardGive TWO reagents to distinguish cyclohexanone from hexanal.arrow_forward
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