ORGANIC CHEMISTRY BOOK& SG/SM
ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
Author: SMITH
Publisher: MCG
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Chapter 12.5, Problem 9P
Interpretation Introduction

Interpretation: Among the given pair of alkynes, the one which has a smaller heat of hydrogenation is to be identified.

Concept introduction: The addition of H2 is known as hydrogenation reaction. This is a syn addition. Alkyne is reduced to alkane. In this reaction, two weak pi bond of alkyne and sigma bond between H2 is broken and four CH bonds are formed.

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Which alkyne has the smaller heat of hydrogenation, HC≡CCH2CH2OH3 orCH3C≡CCH2CH3? Explain your choice.
Complete the following reactions for alkynes. Draw the structure of the product. Name the reactant and the product.
1,4-Pentadiene (CH2=CH-CH2-CH=CH2) is a liquid at room temperature and has a density of 0.66 g/mL and molar mass of 68.12 g/mol. In a laboratory experiment, 3.80 mL of this compound was treated with 4.80 mL of conc. H2SO4 (100% w/w; molar mass 98.08 g/mol). Note that the density of conc. H2SO4 is 1.84 g/mL. The resulting sulfate ester was then treated with 1.20 mL of water (molar mass 18.02 g/mol) affording, after work- up, 2,4-pentanediol (molar mass 104.15 g/mol) as the crude product. The crude product was then purified by simple distillation, which yielded 2.00 g of pure product.  What is the theoretical yield of 2,4-pentanediol expressed in grams? Show calculations.   What is the percentage yield of pure 2,4-pentanediol?

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