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Organic Chemistry

Chapter 21

Organic ChemistryChapter 21

Chapter 21

Problem 21-1
(a)
4-Methylpentanoyl chloride
(b)
Cyclohexylacetamide
(c)
Isopropyl 2-methylpropanoate
(d)
Benzoic anhydride
(e)
Isopropyl cyclopentanecarboxylate
(f)
Cyclopentyl 2-methylpropanoate
(g)
N-Methyl-4-pentenamide
(h)
(R)-2-Hydroxypropanoyl phosphate
(i)
Ethyl 2,3-dimethyl-2-butenethioate
Problem 21-4
(a)
Acetyl chloride > Methyl acetate > Acetamide
(b)
Hexafluoroisopropyl acetate > 2,2,2-Trichloroethyl acetate > Ethyl acetate
Problem 21-5
(a)
CH3CO2– Na+
(b)
CH3CONH2
(c)
CH3CO2CH3 + CH3CO2– Na+
(d)
CH3CONHCH3
Problem 21-7
(a)
Acetic acid + 1-butanol
(b)
Butanoic acid + methanol
(c)
Cyclopentanecarboxylic acid + isopropyl alcohol
Problem 21-9
(a)
Propanoyl chloride + methanol
(b)
Acetyl chloride + ethanol
(c)
Benzoyl chloride + ethanol
Problem 21-10
Benzoyl chloride + cyclohexanol
Problem 21-11
This is a typical nucleophilic acyl substitution reaction, with morpholine as the nucleophile and chloride as the leaving group.
Problem 21-12
(a)
Propanoyl chloride + methylamine
(b)
Benzoyl chloride + diethylamine
(c)
Propanoyl chloride + ammonia
Problem 21-13
(a)
Benzoyl chloride + [(CH3)2CH]2CuLi, or 2-methylpropanoyl chloride + Ph2CuLi
(b)
2-Propenoyl chloride + (CH3CH2CH2)2CuLi, or butanoyl chloride + (H2C = CH)2CuLi
Problem 21-14
This is a typical nucleophilic acyl substitution reaction, with p-hydroxyaniline as the nucleophile and acetate ion as the leaving group.
Problem 21-15
Monomethyl ester of benzene-1,2-dicarboxylic acid
Problem 21-16
Reaction of a carboxylic acid with an alkoxide ion gives the carboxylate ion.
Problem 21-17
LiAlH4 gives HOCH2CH2CH2CH2OH; DIBAH gives HOCH2CH2CH2CHO.
Problem 21-18
(a)
CH3CH2CH2CH(CH3)CH2OH + CH3OH
(b)
PhOH + PhCH2OH
Problem 21-19
(a)
Ethyl benzoate + 2 CH3MgBr
(b)
Ethyl acetate + 2 PhMgBr
(c)
Ethyl pentanoate + 2 CH3CH2MgBr
Problem 21-20
(a)
H2O, NaOH
(b)
Benzoic acid + LiAlH4
(c)
LiAlH4
Problem 21-21
1. Mg; 2. CO2, then H3O+; 3. SOCl2; 4. (CH3)2NH; 5. LiAlH4
Problem 21-25
(a)
Ester
(b)
Acid chloride
(c)
Carboxylic acid
(d)
Aliphatic ketone or cyclohexanone
Problem 21-26
(a)
CH3CH2CH2CO2CH2CH3 and other possibilities
(b)
CH3CON(CH3)2
(c)
CH3CH = CHCOCl or H2C = C(CH3)COCl
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