Concept explainers
Interpretation:
The IUPAC names of each of the given compounds are to be given by using
Concept introduction:
The priority of groups in nomenclature is assigned according to Cahn-Ingold-Prelog (CIP Rule) convention rules:
The higher the
If priority cannot be assigned according to atomic mass, then assign the priority according to first point of difference.
If both the priority groups are on the same side of double-bonded carbon atom, then it is known as
But, if both the priority groups are diagonal to each other, then it is
Rule for R/S Nomenclature:
4B(+)3B(-)2B(+)1B(-)
4B(+) means if 4th priority group is below then from 1 to 2 to 3 if leads a clockwise rotation then its R and if anticlockwise then it is S.
3B(-) means if 3rd priority group is below then from 1 to 2 to 4 if leads a clockwise rotation then its S and if anticlockwise then it is R.
Answer to Problem 1PP
Solution:
Explanation of Solution
a)
The IUPAC name with
Assign the priority to four groups, –Br gets first priority, pentyl group gets second, –Cl gets third, and –H gets fourth. Since both the priority groups are diagonal to each other, it is
Select the longest carbon chain. The parent hydrocarbon chain is pentane and hence pent- will be used and double bond is at the second position. Therefore, pent-1-ene is used.
Chloro and bromo groups are at first position. So, 1-bromo-1-chloropent-1-ene will be used.
Hence, the IUPAC name of the compound will be
b)
The IUPAC name with
Assign the priority to four groups, –I gets first priority, –Br gets second, –Cl gets third, and ethyl group gets fourth. Since both the priority groups are diagonal to each other, it is
Select the longest carbon chain. The parent hydrocarbon chain is butyl and hence but- will be used and double bond is at the first position. Therefore, but-1-ene is used.
Chloro and iodo groups are at first position and bromo group is at second position. So, 2-bromo-1-chloro-1-iodobut-1-ene will be used.
Hence, the IUPAC name of the compound will be
c)
The IUPAC name with
Assign the priority to four groups, 2-methylpropyl gets first priority, both methyl groups get second, and –H gets third. Since both the priority groups are on the same side, it is
Select the longest carbon chain. The parent hydrocarbon chain is hexyl and hence hex- will be used and double bond is at the second position. Therefore, hex-2-ene is used.
There are two methyl groups at third and fifth positions. So, 3,5-dimethylhex-2-ene will be used.
Hence, the IUPAC name of the compound will be
d)
The IUPAC name with
Assign the priority to four groups, –I gets first priority, –Cl gets second, ethyl group gets third, and methyl group gets fourth. Since both the priority groups are on the same side, it is
Select the longest carbon chain. The parent hydrocarbon chain is butyl and hence but- will be used and double bond is at the first position. Therefore, but-1-ene is used.
There is one methyl group at second position, and chloro and iodo groups at first position. So, 1-chloro-1-iodo-2 methylbut-1-ene will be used.
Hence, the IUPAC name of the compound will be
e)
The IUPAC name with
Assign the priority to four groups, 1-methylpropyl gets first priority, both methyl groups get second, and –H gets third. Since both the priority groups are on the same side, it is
Select the longest carbon chain. The parent hydrocarbon chain is hexyl and hence hex- will be used and double bond is at the second position. Therefore, hex-2-ene is used.
There are two methyl groups at third and fourth position. So, 3,4-dimethylhex-2-ene will be used.
Carbon-4 is a chiral carbon. Assigning priority to the groups, 2-butene gets first priority, ethyl gets second, methyl gets third, and hydrogen gets fourth.
Move 1-2-3, it is in anticlockwise direction. So, it is
Hence, the IUPAC name of the compound will be
f)
The IUPAC name can be done using the following steps:
Assign the priority to four groups, –Br gets first priority, –Cl gets second, 1-methylbutyl gets third, and –H gets fourth. Since both the priority groups are on the same side, it is
Select the longest carbon chain. The parent hydrocarbon chain is hexyl and hence hex- will be used and double bond is at the first position. Therefore, hex-1-ene is used.
There is one methyl group at third position, and chloro at second and bromo at first position. So, 1-bromo-2-chloro-3-methylhex-1-ene will be used.
Carbon-3 is a chiral carbon. Assigning priority to the groups, 1-bromo-2-chloroethene gets first priority, propyl gets second, methyl gets third, and hydrogen gets fourth.
Rotate the molecule such that –H is at a horizontal position and then move 1-2-3, it is in anticlockwise direction. So, it is
Hence, the IUPAC name of the compound will be
Want to see more full solutions like this?
Chapter 7 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
- O PRACTICE PROBLEM 8.14 Starting with any needed alkene (or cycloalkene) and assuming you have deuterioace- tic acid (CH3CO,D) available, outline syntheses of the following deuterium-labeled compounds.s el en olad lo nohibbs ad CH3 (a) (CH3)2CHCH2CH,D (b) (CH3),CHCHDCH3 (c) (+ enantiomer) (d) Assuming you also have available BD3:THF and CH3CO2T, can you suggest a synthesis of the following? hab erl (+ enantiomer)he imo (nwond-ben) CH3 H. (asoholea)arrow_forwardPlease answer (a) and (b)arrow_forward(a) Indicate the following alkenes in order of increasing stability. Justify your answers.arrow_forward
- • PRACTICE PROBLEM 8.13 Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration–oxidation. (a) (c) OH (e) CH3 OH AH OH no mobe OH ( (b) (d) (f) OH HT H3 D OH OH HO OHarrow_forwardPlease don't provide handwriting solutionarrow_forwardAnswer ALL parts of this question. The structure shown below is that of the E-isomer of tripolidine, an antihistamine (the E-isomer is more active than the Z-isomer in this capacity): (a) (b) H3C- oto Explain how the Cahn Ingold Prelog sequence rules can be used to rank groups in order of priority, using the four groups attached to the C=C double bond in tripolidine as illustrations. Based on the order of priority of the four groups determined in part (a) of this question, explain why the isomer of tripolidine shown above is defined as the E-isomer. (c) In general terms, explain why this isomer might have different effects in the human body from its geometric isomer.arrow_forward
- Provide the proper systematic IUPAC name for the following compounds. Please assign E, Z, R, and S.arrow_forwardPractice Problem 7.16 When the compound called isoborneol is heated with 9 M sulfuric acid, the product of the reaction is the compound called camphene and not bornylene, as one might expect. Using models to assist you, write a step-by-step mechanism showing how camphene is formed. HO H,O not heat Isoborneol Camphene Bornylenearrow_forwardGive clear detailed Solution with explanation..arrow_forward
- Provide the reagents and solvents (where appropriate) needed to bring about the following transformations. (a) CI (b)arrow_forwardStarting with (S)-2-bromobutane, outline syntheses of each of the following compounds:• PRACTICE PROBLEM 6.19 (a) (R)-CH,CHCH,CH3 (c) (R)-CH,CHCH,CH3 OH bA-(2) ÓCH,CH3 SH muinolue for (b) (R)-CH,CHCH,CH3 (d) (R)-CH,CHCH,CH3 tho betallgo ÓCCH3 ŚCH3arrow_forwardCompare the conformational profile of butane (A) with that of 1,2-dibromoethane (B) While the methyl group is significantly larger than the bromine substituent, butane is found as a mixture of 72% anti and 28% gauche conformers, while compound B consists of 89% anti and 11% gauche conformer. Br Br B A Explain this observation non-verbally.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY