Question

Organic Chemistry Lab Structure & Solubility: Explain how you could distinguish between the following pairs of compounds? Which compounds would be water soluble?

STRUCTURE AND SOLUBILITY Name: Lab Section: I. Esplin how you could distinguish between the following pairs of compounds. Which compounds would be water soluble? 1. Butane and 2-chlorobutane 2. Butane and 1-butanol 3. 1-butanol and 2-butanol 4. 1-butanol and butanoic acid

Answer 1

Q1.

butane = alkane (nonpolar, will not be soluble in water)

2-chlorobutane = haloalkane (polar, will be soluble in water)

Haloalkanes ar emuch reactive

addition of AgNO3 + ethanol + heating will cause precipitation, whereas butane will not

Q2

butane vs. 1-butanol

butane --> will have lower BP --> approx -1-2°C , i.e. it is a gas at room T

butanol --> will have OH group which makes it polar, there will be hydrogne bonding as well, boiling point is higher, 117.7 °C

butane -- alkane (nonpolar, will not be soluble in water)

butnaol = (polar, will be soluble in water)

Q3

1-butanol + 2-butanol

1-butanol = Primary alcohol

2-butanol = secondaru alcohols

both are polar + hydrogen bonded, so expect solubility

addition of oxidant such as permangante will:

oxidize primary carbon to COOH, i.e. carboixlic acid ( terminal group

oxidize seocndary carbon to C=O, i.e ketone

Q4.

1-butanol + butanoic acid

1-butanol has almost a neutral pH; whereas butanoic acid has a lwoer pH, i.e. pH = < 7

butanoic acid will react readily with bases, change of pH is also expected

1-butanol will not likely react with mildbases