Chapter 22, Problem 37PP

(a)

Interpretation Introduction

Interpretation: For a given set of nitrogen containing compounds, the structures have to be drawn using their general or IUPAC names.

Concept Introduction: If ,  and groups are attached to the parent carbon, they are called primary, secondary and tertiary amines respectively.

There are two ways followed to name the compound.  First one is the method of giving general name in which name of the alkyl group followed by amine name is given.  Second one is the method giving IUPAC name in which name of the alkane group followed by amine name is given.

The length of the chain which is having more number of carbon atoms is selected as the parent or main chain.  Other chains are considered as substituents to the main chain.  Position of the substituents should be included in the name.  If one, two, three, four, five, six, etc carbons are activating as the main chain in IUPAC system, then the name of the compound comes as methane, ethane, propane, butane, pentane, hexane, etc. which are the name of alkanes.  If one, two, three, four, five, six, etc carbons are activating as the main chain in general name method, then the name of the compound comes as methyl, ethyl, propyl, butyl, pentyl, hexyl, etc. which are the name of alkyl groups.  If substituent groups are attached to nitrogen atom as in the case of tertiary or secondary amines, the name is given as N-alkyl name of the substituent.

If any configuration is present in the compound, that should be assigned to it while writing the name.  If the compound contains heavier groups on the same side, it gets (Z)-configuration.  If they are on the opposite directions, (E)-configurations result.

If a carbon has four different groups attached to it, that carbon shows a chirality nature.  If that chiral carbon rotates the plane polarized light into a clockwise direction, it gets (R)-isomer.  If that carbon rotates the plane polarized light into a counter-clockwise direction, it gets (S)-isomer.

To find: Categorize the number of alkyl groups attached to nitrogen atom

(b)

Interpretation Introduction

Interpretation: For a given set of nitrogen containing compounds, the structures have to be drawn using their general or IUPAC names.

Concept Introduction: If ,  and groups are attached to the parent carbon, they are called primary, secondary and tertiary amines respectively.

There are two ways followed to name the compound.  First one is the method of giving general name in which name of the alkyl group followed by amine name is given.  Second one is the method giving IUPAC name in which name of the alkane group followed by amine name is given.

The length of the chain which is having more number of carbon atoms is selected as the parent or main chain.  Other chains are considered as substituents to the main chain.  Position of the substituents should be included in the name.  If one, two, three, four, five, six, etc carbons are activating as the main chain in IUPAC system, then the name of the compound comes as methane, ethane, propane, butane, pentane, hexane, etc. which are the name of alkanes.  If one, two, three, four, five, six, etc carbons are activating as the main chain in general name method, then the name of the compound comes as methyl, ethyl, propyl, butyl, pentyl, hexyl, etc. which are the name of alkyl groups.  If substituent groups are attached to nitrogen atom as in the case of tertiary or secondary amines, the name is given as N-alkyl name of the substituent.

If any configuration is present in the compound, that should be assigned to it while writing the name.  If the compound contains heavier groups on the same side, it gets (Z)-configuration.  If they are on the opposite directions, (E)-configurations result.

If a carbon has four different groups attached to it, that carbon shows a chirality nature.  If that chiral carbon rotates the plane polarized light into a clockwise direction, it gets (R)-isomer.  If that carbon rotates the plane polarized light into a counter-clockwise direction, it gets (S)-isomer.

To find: Categorize the number of alkyl groups attached to nitrogen atom

In the given compound (b), three alkyl groups are attached to nitrogen atom.  Therefore, it belongs to tertiary amine.

Decide the given name which is in general name method or IUPAC name method

There are three alkyl groups present in the given name.  Here, the main chain is cyclopropylamine.  Three-membered carbon ring structure is called cyclopropyl group.  So, general name system is followed.

Locate the substituents and draw the corresponding structure for the given name

(c)

Interpretation Introduction

Interpretation: For a given set of nitrogen containing compounds, the structures have to be drawn using their general or IUPAC names.

Concept Introduction: If ,  and groups are attached to the parent carbon, they are called primary, secondary and tertiary amines respectively.

There are two ways followed to name the compound.  First one is the method of giving general name in which name of the alkyl group followed by amine name is given.  Second one is the method giving IUPAC name in which name of the alkane group followed by amine name is given.

The length of the chain which is having more number of carbon atoms is selected as the parent or main chain.  Other chains are considered as substituents to the main chain.  Position of the substituents should be included in the name.  If one, two, three, four, five, six, etc carbons are activating as the main chain in IUPAC system, then the name of the compound comes as methane, ethane, propane, butane, pentane, hexane, etc. which are the name of alkanes.  If one, two, three, four, five, six, etc carbons are activating as the main chain in general name method, then the name of the compound comes as methyl, ethyl, propyl, butyl, pentyl, hexyl, etc. which are the name of alkyl groups.  If substituent groups are attached to nitrogen atom as in the case of tertiary or secondary amines, the name is given as N-alkyl name of the substituent.

If any configuration is present in the compound, that should be assigned to it while writing the name.  If the compound contains heavier groups on the same side, it gets (Z)-configuration.  If they are on the opposite directions, (E)-configurations result.

If a carbon has four different groups attached to it, that carbon shows a chirality nature.  If that chiral carbon rotates the plane polarized light into a clockwise direction, it gets (R)-isomer.  If that carbon rotates the plane polarized light into a counter-clockwise direction, it gets (S)-isomer.

To find: Categorize the number of alkyl groups attached to nitrogen atom

In the given compound (c), only one alkyl group, namely pentane is attached to nitrogen atom.  Therefore, it belongs to primary amine.

Decide the given name which is in general name method or IUPAC name method

There is only one alkane group present in the given name.  It is pentane attached to primary amine named as pentanamine which is the main chain of the given name.  So, IUPAC name system is followed.

Locate the substituents and draw the corresponding structure for the given name

(d)

Interpretation Introduction

Interpretation: For a given set of nitrogen containing compounds, the structures have to be drawn using their general or IUPAC names.

Concept Introduction: If ,  and groups are attached to the parent carbon, they are called primary, secondary and tertiary amines respectively.

There are two ways followed to name the compound.  First one is the method of giving general name in which name of the alkyl group followed by amine name is given.  Second one is the method giving IUPAC name in which name of the alkane group followed by amine name is given.

The length of the chain which is having more number of carbon atoms is selected as the parent or main chain.  Other chains are considered as substituents to the main chain.  Position of the substituents should be included in the name.  If one, two, three, four, five, six, etc carbons are activating as the main chain in IUPAC system, then the name of the compound comes as methane, ethane, propane, butane, pentane, hexane, etc. which are the name of alkanes.  If one, two, three, four, five, six, etc carbons are activating as the main chain in general name method, then the name of the compound comes as methyl, ethyl, propyl, butyl, pentyl, hexyl, etc. which are the name of alkyl groups.  If substituent groups are attached to nitrogen atom as in the case of tertiary or secondary amines, the name is given as N-alkyl name of the substituent.

If any configuration is present in the compound, that should be assigned to it while writing the name.  If the compound contains heavier groups on the same side, it gets (Z)-configuration.  If they are on the opposite directions, (E)-configurations result.

If a carbon has four different groups attached to it, that carbon shows a chirality nature.  If that chiral carbon rotates the plane polarized light into a clockwise direction, it gets (R)-isomer.  If that carbon rotates the plane polarized light into a counter-clockwise direction, it gets (S)-isomer.

To find: Categorize the number of alkyl groups attached to nitrogen atom

In the given compound (d), only one alkyl group is attached to nitrogen atom.  Therefore, it belongs to primary amine.

Decide the given name which is in general name method or IUPAC name method

There is only one alkyl group present in the given name.  It is benzyl group.  So, simple general name system is followed.  If phenyl group is attached to methylene group, it is called benzyl group.

Locate the substituents and draw the corresponding structure for the given name