Propose a synthesis of meso-4,5-octanediol starting from 1-pentyne.Specify the reagents you would use to carry it out. If two or more routes to the same product are possible, show only one of them. Specify reagents using letters from the table, the first reagent on the left.Example: ab.Reagents availableа. 1. ВHg2. CH3 COOHd. 1. Hg(OAc)2, H2O2. NABH,g. H2 / Nie. 1. NaNH2 / NH32. CH3 CH2 CH, Brb. H20, H2SO4. HgSO4h. 2 mol Na / NH3 (I)c. Os04, H2O2f. H2 / Lindlar catalystThe reagents are :

NaNH2/NH3 : Abstracting acidic hydrogen CH3CH2CH2Br : Alkylating agent H2/Lindlar catalyst : Alkyne…

Answered: Propose a synthesis of…

Propose a synthesis of meso-4,5-octanediol starting from 1-pentyne. Specify the reagents you would use to carry it out. If two or more routes to the same product are possible, show only one of them.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 1E

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Concept explainers

Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

Propose a synthesis of meso-4,5-octanediol starting from 1-pentyne.

Specify the reagents you would use to carry it out. If two or more routes to the same product are possible, show only one of them.

Specify reagents using letters from the table, the first reagent on the left.
Example: ab.
Reagents available
а. 1. ВHg
2. CH3 COOH
d. 1. Hg(OAc)2, H2O
2. NABH,
g. H2 / Ni
e. 1. NaNH2 / NH3
2. CH3 CH2 CH, Br
b. H20, H2SO4. HgSO4
h. 2 mol Na / NH3 (I)
c. Os04, H2O2
f. H2 / Lindlar catalyst
The reagents are :

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