Chapter 7.SE, Problem 45AP

Interpretation Introduction

a) -CH₃, -Br, -H, -I.

Interpretation:

To rank -CH₃, -Br, -H, -I according to Cahn-Ingold-Prelog sequence rules.

Concept introduction:

According to Cahn-Ingold-Prelog sequence rules the member that ranks higher can be determined by considering the atomic number of the first atom in each substituent. The atom with highest atomic number gets a higher rank. If a decision cannot be made by considering the atomic number of the first atom in each substituent then the second, third, fourth atoms can be considered until the first difference is found. Multiple bonded atoms are equivalent to the same number of single bonded atoms.

To rank:

The substituents, -CH₃, -Br, -H, -I, according to Cahn-Ingold-Prelog sequence rules.

Answer to Problem 45AP

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -I, -Br, -CH₃, -H.

Explanation of Solution

The first atoms in the substituents given are I, Br, C and CH. Their atomic numbers are 53, 35, 12, 1 respectively. Based on these atomic numbers, the substituents can be ranked in the order -I, -Br, -CH₃, -H.

Conclusion

According to the sequence rules the substituents can be ranked in the order -I, -Br, -CH₃, -H.

Interpretation Introduction

b) -OH, -OCH₃, -H, -CO₂H.

Interpretation:

To rank -OH, -OCH₃, -H, -CO₂H according to Cahn-Ingold-Prelog sequence rules.

Concept introduction:

According to Cahn-Ingold-Prelog sequence rules the member that ranks higher can be determined by considering the atomic number of the first atom in each substituent. The atom with highest atomic number gets a higher rank. If a decision cannot be made by considering the atomic number of the first atom in each substituent then the second, third, fourth atoms can be considered until the first difference is found. Multiple bonded atoms are equivalent to the same number of single bonded atoms.

To rank:

The substituents, -OH, -OCH₃, -H, -CO₂H according to Cahn-Ingold-Prelog sequence rules.

Answer to Problem 45AP

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -OCH₃, -OH, -CO₂H, -H.

Explanation of Solution

Two groups have oxygen as first atom, third one has carbon as the first atom and the fourth one is H. Their atomic numbers are 8, 1, 12 respectively. Both -OH, -OCH₃ have O as the first atom. Hence the second, third and fourth atoms to which they are bonded are to be considered. Oxygen in -OH is bonded to H, while the oxygen in -OCH₃ is bonded to carbon. Hence -OCH₃ ranks higher than -OH. The substituent -CO₂H ranks third and -H the fourth.

Conclusion

According to the sequence rules the substituents can be ranked in the order -OCH₃, -OH, -CO₂H,-H.

Interpretation Introduction

c) -CO₂H, -CO₂CH₃, -CH₂OH, -CH₃.

Interpretation:

To rank -CO₂H, -CO₂CH₃, -CH₂OH, -CH₃ according to Cahn-Ingold-Prelog sequence rules.

Concept introduction:

The member that ranks higher can be determined by considering the atomic number of the first atom in each substituent. The atom with highest atomic number gets a higher rank. If a decision cannot be made by considering the atomic number of the first atom in each substituent then the second, third, fourth atoms can be considered until the first difference is found. Multiple bonded atoms are equivalent to the same number of single bonded atoms.

To rank:

The substituents -CO₂H, -CO₂CH₃, -CH₂OH, -CH₃ according to Cahn-Ingold-Prelog sequence rules.

Answer to Problem 45AP

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CO₂CH₃, -CO₂H, -CH₂OH, -CH₃.

Explanation of Solution

The first atom in all the substituents given is C. Hence the second, third and fourth atoms to which they are bonded are to be considered. Carbon in -CO₂CH₃ is bonded to three oxygens(double bond) out of which one is attached to a carbon. Carbon in COOH is also bonded to three oxygen atom (double bond) out of which one is attached to a hydrogen. Carbon in –CH₂OH is bonded to H, H, O. Carbon in methyl is bonded to H, H, H. Based on the atomic numbers of the differentiating atoms, the substituents can be ranked in the order -CO₂CH₃, -CO₂H, -CH₂OH,-CH₃.

Conclusion

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CO₂CH₃, -CO₂H, -CH₂OH,-CH₃.

Interpretation Introduction

d) -CH₃, -CH₂CH₃, -CH₂CH₂OH, -COCH₃.

Interpretation:

To rank -CH₃, -CH₂CH₃, -CH₂CH₂OH, -COCH₃ according to Cahn-Ingold-Prelog sequence rules.

Concept introduction:

The member that ranks higher can be determined by considering the atomic number of the first atom in each substituent. The atom with highest atomic number gets a higher rank. If a decision cannot be made by considering the atomic number of the first atom in each substituent then the second, third, fourth atoms can be considered until the first difference is found. Multiple bonded atoms are equivalent to the same number of single bonded atoms.

To rank:

The substituents -CH₃, -CH₂CH₃, -CH₂CH₂OH, -COCH₃ according to Cahn-Ingold-Prelog sequence rules.

Answer to Problem 45AP

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -COCH₃, -CH₂CH₂OH, -CH₂CH₃, -CH₃.

Explanation of Solution

The first atom in all the substituents given is C. Hence the second, third and fourth atoms to which they are bonded are to be considered.

Carbon in -COCH₃ is bonded to O, O(double bond), C.

Carbon in -CH₂CH₂OH is bonded to H, H & C attached to H, H, O.

Carbon in –CH₂CH₃ is bonded to H, H & C attached to three hydrogens.

Carbon in methyl is bonded to H, H, H.

Based on the atomic numbers of the differentiating atoms, the substituents can be ranked in the order -COCH₃, -CH₂CH₂OH, -CH₂CH₃, -CH₃.

Conclusion

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -COCH₃, -CH₂CH₂OH, -CH₂CH₃, -CH₃.

Interpretation Introduction

e) -CH=CH₂, -CN, -CH₂NH₂, -CH₂Br.

Interpretation:

To rank -CH=CH₂, -CN, -CH₂NH₂, -CH₂Br according to Cahn-Ingold-Prelog sequence rules.

Concept introduction:

The member that ranks higher can be determined by considering the atomic number of the first atom in each substituent. The atom with highest atomic number gets a higher rank. If a decision cannot be made by considering the atomic number of the first atom in each substituent then the second, third, fourth atoms can be considered until the first difference is found. Multiple bonded atoms are equivalent to the same number of single bonded atoms.

To rank:

The substituents -CH=CH₂, -CN, -CH₂NH₂, -CH₂Br according to Cahn-Ingold-Prelog sequence rules.

Answer to Problem 45AP

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CH₂Br, -CN, -CH₂NH₂, -CH=CH₂.

Explanation of Solution

The first atom in all the substituents given is C. Hence the second, third and fourth atoms to which they are bonded are to be considered.

Carbon in -CH=CH₂, is bonded to C, C(double bond), H.

Carbon in -CN, is bonded to three nitrogens.

Carbon in -CH₂NH₂ is bonded to N, H, H.

Carbon in -CH₂Br is bonded to Br, H, H.

Based on the atomic numbers of the differentiating atoms, the substituents can be ranked in the order -CH₂Br, -CN, -CH₂NH₂, -CH=CH₂.

Conclusion

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CH₂Br, -CN, -CH₂NH₂, -CH=CH₂.

Interpretation Introduction

f) -CH=CH₂, -CH₂CH₃, -CH₂OCH₃, -CH₂OH.

Interpretation:

To rank -CH=CH₂, -CH₂CH₃, -CH₂OCH₃, -CH₂OH according to Cahn-Ingold-Prelog sequence rules.

Concept introduction:

The member that ranks higher can be determined by considering the atomic number of the first atom in each substituent. The atom with highest atomic number gets a higher rank. If a decision cannot be made by considering the atomic number of the first atom in each substituent then the second, third, fourth atoms can be considered until the first difference is found. Multiple bonded atoms are equivalent to the same number of single bonded atoms.

To rank:

The substituents -CH=CH₂, -CH₂CH₃, -CH₂OCH₃, -CH₂OH according to Cahn-Ingold-Prelog sequence rules.

Answer to Problem 45AP

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CH₂OCH₃, -CH₂OH, -CH=CH₂, CH₂CH₃.

Explanation of Solution

The first atom in all the substituents given is C. Hence the second, third and fourth atoms to which they are bonded are to be considered.

Carbon in -CH=CH₂, is bonded to C, C(Double bond), H.

Carbon in -CH₂CH₃ is bonded to C, H, H.

Carbon in -CH₂OCH₃ is bonded to H, H, O attached to a carbon.

Carbon in -CH₂OH is bonded to H, H, O attached to a hydrogen.

Based on the atomic numbers of the differentiating atoms, the substituents can be ranked in the order -CH₂OCH₃, -CH₂OH, -CH=CH₂, CH₂CH₃.

Conclusion

According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CH₂OCH₃, -CH₂OH, -CH=CH₂, CH₂CH₃.