5048

Show how each of the following compounds could be prepared starting with a carbonyl compound:

(a)

(b) 3-pentanol

(c) triphenylcarbinol

5054

Indicate the major organic product(s) formed when a-methylcinnamaldehyde (2-methyl-3-phenylpropenal) reacts with each of the following reagents:

(a) C₂H₅OH / H⁺

(b) LiAlH₄ in ether

(c) HSCH₂CH₂SH / BF₃

5061

Compound A is converted to compound E by the sequence of reactions outlined below. The IR spectrum of E shows C-H stretching absorptions at about 3030 cm^–1 (3.3 µm), 2900 cm^–1 (3.5 µm) and a weak peak at 2160 cm^–1 (4.6 µm). The ¹H NMR spectrum of E has singlets at 1.7, 2.7, and 7.0 ppm. with peak relative areas of 1:2:2. Suggest structures for compounds B through E.

5137

A sample of 3-methyl-2-heptanol was treated with successive portions of aqueous sodium hypochlorite solution until no further reaction occurred. The solution was diluted with water and extracted with several portions of ether. The combined ether extracts were washed with sodium bisulfite solution, then water, and finally dried over anhydrous magnesium sulfate. The filtered ether solution was evaporated, leaving a residue, which distilled at 166-170°.

(a) Write an equation which shows the course of reaction in the experiment above.

(b) What is the purpose of the bisulfite wash in the workup procedure?

5181

Using the reagents indicated, write the equations for each synthesis described below:

(a) 2-Butanol from acetaldehyde and other reagents

(b) 1-Butanol from ethyl bromide and other reagents

(c) The major product(s) from acetone and sodium acetylide after hydrolysis in aqueous ammonium chloride

(d) Isopropyl alcohol from acetone

(e) Wolff-Kishner reduction of 2-butanone

5253

State whether the following statements or equations are true or false. If any part of a statement is not true or any part of an equation is incorrect, then the item is false.

(a) one can distinguish between the two structures in the allylic rearrangement shown below by use of ¹³C and/or ¹H magnetic resonance spectroscopy

(b) the Newman structures shown below are diastereomers

(c)

(d)