Concept explainers
Videos
Give IUPAC names for the following compounds:
a)
Interpretation:
To give the IUPAC name of the compound given.
Concept introduction:
Alcohols are named as derivatives of the parent alkane using the suffix–ol. The longest carbon chain containing the hydroxyl group is chosen and the parent name is derived by replacing the ending–e with–ol. The akane chain is numbered beginning at the end nearer to the hydroxyl group. The substituents are numbered according to their position on the chain. The name is written listing the substituents in the alphabetical order and indicating the position to which –OH is bonded.
If the compound is chiral then there can be two types of arrangements of the four groups attached to the chiral carbon, R and S. The four groups are arranged in the order of priority as 1,2,3 and 4 following sequence rules. The molecule is viewed by orienting the group of lowest priority (4) points away from the observer. If the arrangement of highest to second highest to third highest is clockwise the R configuration is assigned. If the arrangement is anticlockwise then S configurationis assigned.
To give:
The IUPAC name of the compound given.
Answer to Problem 20VC
The compound given is
Its IUPAC name is (R) - 5 methylhexan-3-ol.
Explanation of Solution
The name of the compound indicates the presence of a six carbon straight chain with –OH on C3 and a methyl group on C5. Further the molecule is chiral. The groups –OH (highest ranking), -CH2CH(CH3)2(second highest ranking) and -CH2CH3(third highest ranking) are arranged around the chiral carbon in clockwise arrangement. Hence R configuration is assigned.
The compound given is
Its IUPAC name is (R) - 5 methylhexan-3-ol.
b)
Interpretation:
To give the IUPAC name of the compound given.
Concept introduction:
In naming cyclic alcohols the parent name is derived from the cycloalkene ring by replacing–e of the cycloalkene with–ol. The ring is numbered from the carbon with –OH in such a way that lowest number possible is given to the carbons with substituents.
A cis 1,3-disubstituted cycloalkane has the two substituent groups in a diequatorial arrangement.
To give:
The IUPAC name of the compound given.
Answer to Problem 20VC
The compound given is
Its IUPAC name is cis-3-methylcyclohexanol.
Explanation of Solution
The structure shows that the compound contains a cyclohexane ring with a –OH and methyl groups in diequatorial positions on C1 and C3. Hence it is a cis-isomer.
The compound given is
Its IUPAC name is cis-3-methylcyclohexanol.
c)
Interpretation:
To give the IUPAC name of the compound given.
Concept introduction:
Alcohols are named as derivatives of the parent alkane using the suffix–ol. The longest carbon chain containing the hydroxyl group is chosen and the parent name is derived by replacing the ending–e with–ol. He akane chain is numbered beginning at the end nearer to the hydroxyl group. The substituents are numbered according to their position on the chain. The name is written listing the substituents in the alphabetical order and indicating the position to which –OH is bonded.
If the compound is chiral then there can be two types of arrangements of the four groups attached to the chiral carbon, R and S. The four groups are arranged in the order of priority as 1,2,3 and 4 following sequence rules. The molecule is viewed by orienting the group of lowest priority (4) points away from the observer. If the arrangement of highest to second highest to third highest is clockwise the R configuration is assigned. If the arrangement is anticlockwise then S configurationis assigned.
To give:
The IUPAC name of the compound given.
Answer to Problem 20VC
The compound given is
Its IUPAC name is (S)-1-cyclopentylethanol.
Explanation of Solution
The structure shows that the compound contains a two carbon straight chain with –OH and a cyclopentyl groups on C1.
The four groups, -OH(Highest priority), Cyclopentyl (second highest priority), methyl (third highest priority) attached to C1 are arranged anticlockwise when viewed away from hydrogen (fourth priority). Hence S configuration is assigned.
The compound given is
Its IUPAC name is (S)-1-cyclopentylethanol.
d)
Interpretation:
To give the IUPAC name of the compound given.
Concept introduction:
Hydroxybenzenes are named as derivatives of phenol. If the ring contains other substituent also the ring is numbered from the carbon with –OH in such a way that lowest number possible is given to the carbon with the substituent. While writing the name the substituents are arranged in the alphabetical order.
To give:
The IUPAC name of the compound given.
Answer to Problem 20VC
The compound given is.
Its IUPAC name is 4-methyl-3-nitrophenol.
Explanation of Solution
The structure of the compound shows a benzene ring with –OH on C1, a nitro group on C3 and a methyl group on C4.
The compound given is.
Its IUPAC name is 4-methyl-3-nitrophenol.
Want to see more full solutions like this?
Chapter 17 Solutions
Organic Chemistry
- Draw and name all phenols with the formula C7H8O.arrow_forwardWrite IUPAC names for these compounds. (a) Cl (b) (c) NO2 COOH COOH OHarrow_forwardArrange these compounds in order of increasing boiling point (values in C are 42, 24, 78, and 118). (a) CH3CH2OH (b) CH3OCH3 (c) CH3CH2CH3 (d) CH3COOHarrow_forward
- Terpineol has 5 isomers. Write their structures and describe why chemically (optically) they receive those names. Number the carbons for a better description.arrow_forwardWrite the correct IUPAC name for each of the following structures (3 marks per structure, 1 mark deduction per error):arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) a) Given 7.70 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100% yield? b) A chemist ran the reaction and obtained 5.25 g of ethyl butyrate. What was the percent yield? c) The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 7.70 g of butanoic acid and excess ethanol?arrow_forward
- Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l) Given 8.50 g of butanoic acid and excess ethanol, how many grams of ethyl butyrate would be synthesized, assuming a complete 100%yield? Express your answer in grams to three significant figures.arrow_forwardEthyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.arrow_forwardWhat is the IUPAC name for the compound shown? Он IUPAC name:arrow_forward
General, Organic, and Biological ChemistryChemistryISBN:9781285853918Author:H. Stephen StokerPublisher:Cengage Learning
Organic And Biological ChemistryChemistryISBN:9781305081079Author:STOKER, H. Stephen (howard Stephen)Publisher:Cengage Learning,
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning