Name: Glaizelle T. Leonoras Subject: Organic Chemistry

Course: Ph. D. in Science Education (Physical Science) Professor: Vilma F. Templora, Ph.D.

Problem Set 3 on Alkynes

III. Give the steps on how to obtain the products

1.

NaNH2, NH3 H , Pd / C
CH3CH2C C H CH3CH2Br CH3CH2C CCH2CH3 2 or
CH3CH2CH CHCH2CH3
Li / NH3 BH3, THF
Hg(OAc)2H2O/THF or H2O2, NaOH, H2O
NaBH4

OH

CH3CH2CHCH2CH2CH3
IV. Using acetylene and any alkyl halides as starting materials, synthesize the following compounds. More than one step may be required. Show all reagents and all
intermediate compounds in your synthetic scheme.

1.

NaNH2 NH3
HC CH CH3CH2CH2CH2CH2I
HC CCH2CH2CH2CH2CH3

HgSO4, H2SO4
H2 O

CH3CCH2CH2CH2CH2CH3

2.

NaNH2, NH3 H / Lindlar

HC CH
CH3I
HC CCH2 3or H2C CHCH3
Li / NH3
Cl2
CCl4

Cl
Cl
3.

NaNH2, NH3 NaNH2 NH3

HC CH CH3C CH CH3C CCH3
CH3I CH3I H2C KMnO4
H3O+

2H3C C OH

4.

NaNH2, NH3 H2
HC CH HC CCH2CH2CH3 Lindlar catalyst
HC CHCH2CH2CH3
CH3CH2CH2I
HBr
ether

Br

CH3CHCH2CH2CH3