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문제 20a
Draw the following sugars using Haworth projections:
a. β-D-galactopyranose
문제 20b
Draw the following sugars using Haworth projections:
b. α-D-tagatopyranose
문제 21a1
Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.
(a) propiophenone from propionic acid (using alkylation of the acid)
문제 21b
Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.
(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid
문제 22
Propose a mechanism for the reaction of benzoic acid with oxalyl chloride. This mechanism begins like the thionyl chloride reaction, to give a reactive mixed anhydride. Nucleophilic acyl substitution by chloride ion gives a tetrahedral intermediate that eliminates a leaving group, which then fragments into carbon dioxide, carbon monoxide, and chloride ion.
문제 23a
Propose mechanisms for the nucleophilic acyl substitutions to form ethyl benzoate as shown on the previous page.
문제 23b
Propose mechanisms for the nucleophilic acyl substitutions to form N-methylacetamide as shown on the previous page.
문제 24a
Show how you would use an acid chloride as an intermediate to synthesize.
(a) N-phenylbenzamide (PhCONHPh) from benzoic acid and aniline.
문제 24b
Show how you would use an acid chloride as an intermediate to synthesize
(b) phenyl propionate (CH3CH2COOPh) from propionic acid and phenol.
문제 25a,b
Give the IUPAC names of the following compounds.
(a) CH3CH2C≡CCOOH
(b) CH3CH(NH2)CH(OH)COOH
문제 25c,d
Give the IUPAC names of the following compounds.
(c) (CH3)2C=CHCOOH
(d)
문제 25e,f
Give the IUPAC names of the following compounds.
(e)
(f)
문제 27f-i
Draw the structures of the following compounds.
(f) salicylic acid
(g) zinc undecanoate (athlete's-foot powder)
(h) sodium benzoate (a food preservative)
(i) sodium fluoroacetate (Compound 1080, a controversial coyote poison)
문제 28
Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline
문제 29c,d
Arrange each group of compounds in order of increasing basicity.
c. sodium benzoate, sodium ethoxide, and sodium phenoxide
d. pyridine, sodium ethoxide, and sodium acetate
문제 30a,b,c
Predict the products (if any) of the following acid–base reactions.
(a) acetic acid + ammonia
(b) phthalic acid + excess NaOH
(c) p-toluic acid + potassium trifluoroacetate
문제 30d,e
Predict the products (if any) of the following acid–base reactions.
(d) α-bromopropionic acid + sodium propionate
(e) benzoic acid + sodium phenoxide
문제 31
Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.
문제 32
Arrange each group of compounds in order of increasing acidity.
(a) phenol, ethanol, acetic acid
(b) p-toluenesulfonic acid, acetic acid, chloroacetic acid
(c) benzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid
(d) butyric acid, α-bromobutyric acid, β-bromobutyric acid
(e)
문제 34a,b
Given the structure of ascorbic acid (vitamin C):
(a) Is ascorbic acid a carboxylic acid?
(b) Compare the acid strength of ascorbic acid (pKa = 4.71) with acetic acid.
문제 34c,d
Given the structure of ascorbic acid (vitamin C):
(c) Predict which proton in ascorbic acid is the most acidic.
(d) Draw the form of ascorbic acid that is present in the body (aqueous solution, pH = 7.4)
문제 36a
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(a) trans-1-bromobut-2-ene → trans-pent-3-enoic acid (two ways)
문제 36b
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(b) hex-3-ene → propanoic acid
문제 36c
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(c) but-2-enal → but-2-enoic acid
문제 36d
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(d) hexanoic acid → hexanal
문제 36e
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(e)
문제 36f
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(f)
문제 36g
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(g)
문제 36h
Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).
(h)
문제 37a
Predict the products and propose mechanisms for the following reactions.
(a)
