Concept explainers
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
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.
According to the sequence rules the substituents can be ranked in the order -I, -Br, -CH3, -H.
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.
According to the sequence rules the substituents can be ranked in the order -OCH3, -OH, -CO2H,-H.
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.
According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CO2CH3, -CO2H, -CH2OH,-CH3.
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.
According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -COCH3, -CH2CH2OH, -CH2CH3, -CH3.
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.
According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CH2Br, -CN, -CH2NH2, -CH=CH2.
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.
According to Cahn-Ingold-Prelog sequence rules the substituents can be ranked in the order -CH2OCH3, -CH2OH, -CH=CH2, CH2CH3.
Want to see more full solutions like this?
Chapter 7 Solutions
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
- What is the IUPAC name of the following compound? CH₂CH₂ H CI H₂CH₂C H CH₂ Selected Answer: O (35,4R)-4 chloro-3-ethylpentane Correctarrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. I I I H Select to Add Arrows HCI, CH3CH2OHarrow_forward
- Curved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and the follow the arrows to draw the intermediate and product in this reaction or mechanistic step(s).arrow_forwardCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the intermediates and product of the following reaction or mechanistic step(s).arrow_forwardCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the arrows to draw the intermediate and the product in this reaction or mechanistic step(s).arrow_forward
- Look at the following pairs of structures carefully to identify them as representing a) completely different compounds, b) compounds that are structural isomers of each other, c) compounds that are geometric isomers of each other, d) conformers of the same compound (part of structure rotated around a single bond) or e) the same structure.arrow_forwardGiven 10.0 g of NaOH, what volume of a 0.100 M solution of H2SO4 would be required to exactly react all the NaOH?arrow_forward3.50 g of Li are combined with 3.50 g of N2. What is the maximum mass of Li3N that can be produced? 6 Li + N2 ---> 2 Li3Narrow_forward
- 3.50 g of Li are combined with 3.50 g of N2. What is the maximum mass of Li3N that can be produced? 6 Li + N2 ---> 2 Li3Narrow_forwardConcentration Trial1 Concentration of iodide solution (mA) 255.8 Concentration of thiosulfate solution (mM) 47.0 Concentration of hydrogen peroxide solution (mM) 110.1 Temperature of iodide solution ('C) 25.0 Volume of iodide solution (1) used (mL) 10.0 Volume of thiosulfate solution (5:03) used (mL) Volume of DI water used (mL) Volume of hydrogen peroxide solution (H₂O₂) used (mL) 1.0 2.5 7.5 Time (s) 16.9 Dark blue Observations Initial concentration of iodide in reaction (mA) Initial concentration of thiosulfate in reaction (mA) Initial concentration of hydrogen peroxide in reaction (mA) Initial Rate (mA's)arrow_forwardDraw the condensed or line-angle structure for an alkene with the formula C5H10. Note: Avoid selecting cis-/trans- isomers in this exercise. Draw two additional condensed or line-angle structures for alkenes with the formula C5H10. Record the name of the isomers in Data Table 1. Repeat steps for 2 cyclic isomers of C5H10arrow_forward
