Draw the following sugars using Haworth projections:

a. β-D-galactopyranose

Draw the following sugars using Haworth projections:

b. α-D-tagatopyranose

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)

Show how the following ketones might be synthesized from the indicated acids, using any necessary reagents.

(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid

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.

Propose mechanisms for the nucleophilic acyl substitutions to form ethyl benzoate as shown on the previous page.

Propose mechanisms for the nucleophilic acyl substitutions to form N-methylacetamide as shown on the previous page.

Show how you would use an acid chloride as an intermediate to synthesize.

(a) N-phenylbenzamide (PhCONHPh) from benzoic acid and aniline.

Show how you would use an acid chloride as an intermediate to synthesize

(b) phenyl propionate (CH₃CH₂COOPh) from propionic acid and phenol.

Give the IUPAC names of the following compounds.

(a) CH₃CH₂C≡CCOOH

(b) CH₃CH(NH₂)CH(OH)COOH

Give the IUPAC names of the following compounds.

(c) (CH₃)₂C=CHCOOH

(d)

Give the IUPAC names of the following compounds.

(e)

(f)

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)

Show how you would use extractions with a separatory funnel to separate a mixture of the following compounds: benzoic acid, phenol, benzyl alcohol, aniline

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

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

Predict the products (if any) of the following acid–base reactions.

(d) α-bromopropionic acid + sodium propionate

(e) benzoic acid + sodium phenoxide

Rank the following isomers in order of increasing boiling point, and explain the reasons for your order of ranking.

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)

Given the structure of ascorbic acid (vitamin C):

(a) Is ascorbic acid a carboxylic acid?

(b) Compare the acid strength of ascorbic acid (pK_a = 4.71) with acetic acid.

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)

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)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(b) hex-3-ene → propanoic acid

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(c) but-2-enal → but-2-enoic acid

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(d) hexanoic acid → hexanal

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(e)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(f)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(g)

Show how you would accomplish the following syntheses efficiently (you may use any necessary reagents).

(h)

Predict the products and propose mechanisms for the following reactions.

(a)