Chem221 Organic Chemistry, Winter 2012 Problem set 5 Chapter 13. Alkynes. Due at 10:30am on Tuesday 02/14/2012.

Professor Jun Yin

1. Starting from ethyne and organic compounds with two or less carbons, provide scheme to synthesize the following. You may use any other needed reagents. (a) Propyne. (b) 1-Butyne. (c) 2-Butyne. (d) cis-2-Butene. (e) trans-2-Butene. (f) 1-Pentyne. (g) 2-Hexyne. (h) (Z)-2-Hexene. (i) (E)-2-Hexene. (j) 3-Hexyne. (k)

(l)

2. Compounds A, B and C all have the general formula C6H10. All three compounds decolorize bromine in CCl4. Compound A has an IR absorption at 3300 cm-1 while B and C do not. A and B both yield hexane when they are treated with excess hydrogen in the presence of a platinum catalyst. Under the same condition, C only absorbs one molar equivalent of hydrogen and gives a product of the formula C6H12. A reacts with hot potassium permangnate and the resulting solution contains npentanoic acid. Similar treatment on B gives propionic acid and on C gives 1,6-hexadionic acid. Based on this information, please provide the structures of A, B, and C. 3. Provide the products of the following reactions.

Chem221 Organic Chemistry, Winter 2012

Professor Jun Yin

4. Please provide schemes to accomplish the following synthesis.

Chem221 Organic Chemistry, Winter 2012

Professor Jun Yin

5. Please provide mechanisms of the following transformation.

Chem221 Organic Chemistry, Winter 2012

Professor Jun Yin

6. Please provide the structures of the following organic compounds based on their spectroscopy. (a) C8H14O2

Chem221 Organic Chemistry, Winter 2012

Professor Jun Yin

(b) C6H6O

Chem221 Organic Chemistry, Winter 2012 (c) C5H6O

Professor Jun Yin