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32.5.21: Chapter 21

  • Page ID
    460332
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    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 21-2
    (a) The structure of phenyl benzoate shows two phenyl groups single-bonded to the carbonyl carbon.
    (b) The structure of N-ethyl-N-methylbutanamide shows a four-carbon chain, C 1 of which is a carbonyl group to which a methyl and ethyl substituted nitrogen is attached.
    (c) The structure of 2,4-dimethylpentanoyl chloride shows a five-carbon chain, C 1 of which is a carbonyl group to which a chlorine atom is attached. Methyl groups are attached to C 2 and C 4.
    (d) The structure of methyl 1-methylcyclohexanecarboxylate shows a methyl ester and methyl group both attached to the same carbon of a cyclohexane ring.
    (e) The structure of ethyl 3-oxopentanoate shows a five-carbon chain, C 1 and C 3 of which are carbonyl groups. Alttached to the carbonyl group at C 1 is an ethoxy group.
    (f) The structure of methyl-p-bromobenzenethioate shows a carbonyl group to which is attached a methyl sylfide group and a benzene ring with a bromine atom in the 4-position.
    (g) The structure of formic propanoic anhydride shows two carbonyl groups linked by an oxygen atom. A hydrogen atom is attached to one of the carbonyls and an ethyl group to the other.
    (h) The structure of cis-2-methylcyclopentanecarbonyl bromide shows a cyclopentane ring with a methyl group drawn as a wedge on one carbon and a carbonyl group on the next carbon of the ring, drawn as a wedge. Also attached to the carbonyl group is a bromine atom.
    Problem 21-3 Methoxide ion adds to the carbonyl carbon of benzoyl chloride, forming an intermediate, which on elimination of a chloride ion, gives the product methyl benzoate.
    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 21-6 Methyl-2-cyclopentylacetate reacts with hydroxide ions. The product is not shown. The carboxylate analog of methyl-2-cyclopentylacetate reacts with methoxide ions and again the product is not shown.
    Problem 21-7
    (a) Acetic acid + 1-butanol
    (b) Butanoic acid + methanol
    (c) Cyclopentanecarboxylic acid + isopropyl alcohol
    Problem 21-8 The lactone structure comprises of a six-membered ring containing a carbonyl group with an oxygen atom next to it in the ring.
    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 21-22 The reaction shows the mechanism for the reaction of an ester attached to adenosine and a thiol forming acetyl coenzyme A, and a product in which a phosphate group is bonded to adenosine.
    Problem 21-23
    (a) The structure shows a repeating unit of O C H 2 C H 2 C H 2 O C H 2 C H 2 C H 2 with subscript n.
    (b) The structure shows a repeating unit of O C H 2 C H 2 O C O (C H 2) 6 C O with subscript n.
    (c) The repeating unit of a polymer in brackets with N H bonded to six methylene bonded to N H bonded to a carbonyl group which itself is bonded to four methylene units and then another carbonyl group.
    Problem 21-24 The structure shows a repeating unit of N H (C H 2) 6 N H C O (C H 2) 4 C O in parentheses with subscript n.
    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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