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PS 3 Cont

The document is a problem set from an organic chemistry Ph.D. course. It contains 4 synthesis problems involving reactions of acetylene and alkyl halides. The first problem asks for the steps to obtain products from a series of reactions. The other 3 problems ask the student to synthesize specific compounds from acetylene and alkyl halides, showing all reagents and intermediates.

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Denisse Leonoras-Paterson
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71 views3 pages

PS 3 Cont

The document is a problem set from an organic chemistry Ph.D. course. It contains 4 synthesis problems involving reactions of acetylene and alkyl halides. The first problem asks for the steps to obtain products from a series of reactions. The other 3 problems ask the student to synthesize specific compounds from acetylene and alkyl halides, showing all reagents and intermediates.

Uploaded by

Denisse Leonoras-Paterson
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as DOCX, PDF, TXT or read online on Scribd
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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

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