TOPIC: 18. Aldehydes and Ketones

SUBTOPIC: 192. General

5067

Refer to the reactions below to answer the questions which follow:

(a)

(b)

(c)

(d)

Classify the overall reaction operationally (eg., addition, substitution, etc.)

(a)_____________________________________

(b)_____________________________________

(c)_____________________________________

(d)_____________________________________

5068

For each case below indicate whether or not you predict the tetracoordinate compound to be thermodynamically stable with respect to the related tricoordinate species formed by an elimination reaction. Does a pattern emerge regarding stability?

(a)

(b)

(c)

(d)

5069

Predict the main organic product(s) in each of the following reactions Write the structure of the product(s) in the box at the right.

(a)

(b)

(c)

5136

Compound 2 is a clear, pungent-smelling liquid which boiled at 145±7° (micro boiling point). It was insoluble in water or a solution of 5% HCl and 5% NaOH, but it reacted with concentrated H₂SO₄. It did not react with ammoniacal silver nitrate or KMnO₄ at room temperature, and gave fumes slowly when it was treated with bromine in CCl₄. It gave a dense yellow solid when shaken with NaOH / KI / I₂ reagent, and gave a flocculent yellow precipitate with 2,4-dinitrophenylhydrazine reagent. When treated with semicarbazone hydrochloride it formed a solid which, after recrystallization from ethanol, melted at 121-123°. It displayed its most prominent infrared absorption at 1735 cm^–1. What conclusions are justified from the data above? Make a reasonable guess regarding the structure or part-structure of this compound.

5183

Suggest a qualitative chemical test that could be used to distinguish between the following pairs of isomeric compounds. Indicate what you would do and see. Complete chemical equations are not required.

(a)

(b)

(c)

(d)

(e)

5237

Complete the following equations by supplying, in the box provided, the missing reagent(s)/reactant(s)/principle organic product(s) as required:

(a)

(b)

(c)

(d)

(e)

(f)

(g)

(h)

(i)

(j)

5351

Complete the following syntheses by supplying missing reagents, products, or intermediates, as required. More than one step may be involved.

(a)

(b)

(c)

(d)

1,3-diphenyl-2-propene-1-one and phenylmagnesium bromide in ether