Chapter 23, Problem 48R

To determine

To draw: A substituted hydrocarbon with six carbon atoms, hydroxyl groups, single, double, and triple bonds, and amino group.

Explanation of Solution

Introduction:

An organic compound at given conditions can be drawn considering the possible number of bonds an atom can form. For example, C can form maximum of 4 bonds. These can be 4 single bonds, 2 double bonds and 1 triple and 1 single bond. Now, carbon with triple bond can only form an additional single bond thus, triple bond is always at terminal position.

From the name, hydrocarbons are formed from hydrogen and carbon. Now, substituted hydrocarbons means there is a main chain of carbon and hydrogen and different groups are substituted on it.

To determine the structure, first identify types of atoms present in the compound. According to the question, there are 6 carbon atoms, 1 -OH group and 1 $-{\text{NH}}_{\text{2}}$ group. Also, there are all types of bonds that is single, double and triple.

All the 6 carbon atoms can be drawn as a main chain. Triple bond is only possible at terminal position and all the other groups can take any position such that valency of all the atoms gets satisfied. There are number of possible structures and one of them is as follows:

  

Conclusion:

Thus, the structure of substituted hydrocarbon as per the given information is as follows: