Question

Rank the compounds in each of the following series in order of increasing oxidation level:

1. 
2. 

Short answer

1. $C{H}_{3}C{H}_{2}CH=C{H}_2<C{H}_{3}CH=CHC{H}_3<C{H}_{3}C{H}_{2}C{H}_{2}CHO<C{H}_{3}C{H}_{2}C{H}_{2}COOH$
   
2. $C{H}_{3}C{H}_{2}C{H}_{2}N{H}_2<C{H}_{3}C{H}_{2}C{H}_{2}Br=BrC{H}_{2}C{H}_{2}C{H}_{2}CI<C{H}_{3}COC{H}_{2}CI$
   

Step-by-step solution

Oxidation level

The oxidation level in an organic compound is calculated by using the oxidation number of carbon atoms, counting the number of oxygen atoms, and by counting the number of hydrogen atoms.

a) Order of increasing oxidation level

In this case, the oxidation level of a molecule is calculated by using the formula as follows:

Oxidation level = Number of bonds bonded to atoms more electronegative than

carbon+ Number of pi bonds to other carbon atoms

For

$C{H}_{3}CH=CHC{H}_3$the OL is -1

$C{H}_{3}C{H}_{2}CH=C{H}_2$ the OL is -2

$C{H}_{3}C{H}_{2}C{H}_{2}CHO$the OL is +2

$C{H}_{3}C{H}_{2}C{H}_{2}COOH$the OL is 3

Thus, the order of increasing oxidation levels is as follows:

$C{H}_{3}C{H}_{2}CH=C{H}_2<C{H}_{3}CH=CHC{H}_3<C{H}_{3}C{H}_{2}C{H}_{2}CHO<C{H}_{3}C{H}_{2}C{H}_{2}COOH$

b) Order of increasing oxidation level

$C{H}_{3}C{H}_{2}C{H}_{2}N{H}_2$the OL is -2

$C{H}_{3}C{H}_{2}C{H}_{2}Br$the OL is +1

$C{H}_{3}COC{H}_{2}CI$the OL is +2

$BrC{H}_{2}C{H}_{2}C{H}_{2}CI$the OL is +1

Thus, the order of increasing oxidation levels is as follows:

$C{H}_{3}C{H}_{2}C{H}_{2}N{H}_2<C{H}_{3}C{H}_{2}C{H}_{2}Br=BrC{H}_{2}C{H}_{2}C{H}_{2}CI<C{H}_{3}COC{H}_{2}CI$