
(a)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
(a)

Explanation of Solution
The given compound is as follows.
Let’s given numbering to this compound as follows,
The parent chain contains 9 carbon atoms; in the fifth carbon atom a ketone functional group is attached.
Thus, according to IUPAC this compound can be named as 5-Nonanone.
(b)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups,
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
(b)

Explanation of Solution
The given compound is as follows.
Let’s write give the numbering to this compound.
This parent ring has five carbon atoms; a methyl group was attached to the second carbon atom. Therefore, according to the IUPAC rules, the compound can be named as
Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,
The numbering follows an anti-clock wise direction and so molecule is in as S configuration.
Thus, the compound name can be written as
(c)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
(c)

Explanation of Solution
The given compound is as follows.
Let’s give the numbering to the given compound.
The parent hydrocarbon chain has two functional groups and they are
(d)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
(d)

Explanation of Solution
The given compound is as follows.
Let’s write give the numbering to this compound.
This parent chain has three carbon atoms; a methyl group was attached to the second carbon atom and hydroxyl group was attached to the third carbon atom. Therefore, according to the IUPAC rules, the compound can be named as 3-Hydroxy-2-methyl-propanal.
Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,
The numbering of substituents on the chiral center follows clock wise direction and so molecule is in R configuration.
Thus, the compound name can be written as (R)-3-Hydroxy-2-methyl-propanal.
(e)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
(e)

Explanation of Solution
The given compound is as follows.
Let’s give the numbering to the given compound.
A phenyl ring is attached to the first carbon atom in the three membered parent carbon chains. According to IUPAC the aldehyde group has higher priority. Thus the compound can be named as 1-phenyl-1-propanone.
(f)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
R and S nomenclature: it is used to assign the molecule using CIP (Cahn-Ingold-Prelog) rules.
The CIP rules are as follows:
Select the chiral carbon and assign the numbers according to the decreasing atomic mass of atoms attached to it.
If the numbering follows clockwise direction then the molecule is termed as R and if it follows anti-clockwise direction then molecule is termed as S.
(f)

Explanation of Solution
The given compound is as follows.
Let’s write give the numbering to this compound.
This parent ring has six carbon atoms; a hydroxyl (–OH) and a phenyl ring were attached to the first and fifth carbon atoms in the parent chain respectively. Therefore, according to the IUPAC rules, the compound can be named as 5-Hydroxy-1-phenyl-3-hexanone.
Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,
The numbering follows an anti-clock wise direction and so molecule is in as S configuration.
Thus, the compound name can be written as (S)-5-Hydroxy-1-phenyl-3-hexanone.
(g)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
(g)

Explanation of Solution
The given compound is as follows.
Let’s give the numbering to the given compound.
The parent hydrocarbon ring has five carbon atoms. A propyl group was attached to the second carbon atom in the ring and two ketone groups were present in first and third carbon atom respectively. Thus the compound can be named as
(h)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
(h)

Explanation of Solution
The given compound is as follows.
Let’s give the numbering to the given compound.
The parent hydrocarbon chain has five carbon atoms with two aldehydes on both ends. Thus according to IUPAC the compound can be named as pentanedial.
(i)
Interpretation:
The given compound’s IUPAC name has to be determined and the relevant stereochemistry should be specified.
Concept introduction:
The functional group in the aldehydes and Ketones are carbonyl group.
Naming Aldehydes:
Aldehydes have at least one hydrogen attached to the carbonyl carbon atom.
The IUPAC naming of aldehydes is obtained by replacing the final "e" on the name of the parent hydrocarbon with "al".
For example:
Naming Ketones:
The IUPAC name of a ketones are obtained by replacing the "e" on the end of the parent hydrocarbon with "one".
Only few ketones have common name.
For example:
Naming of compounds with two functional groups;
If a compound has two functional groups, the one with lower priority is indicated by a prefix and another with the higher priority by a suffix.
(i)

Explanation of Solution
The given compound is as follows.
Let’s give the numbering to the given compound.
The parent hydrocarbon chain has two functional groups and they are bromine and ketone. According to IUPAC the bromine has higher priority. Thus the compound can be named as 2-bromo-3-pentanone.
Here, this compound has a chiral center (it is highlighted as *); its configuration can be specified as follows,
The numbering follows a clock wise direction and so molecule is in R configuration.
Thus, the compound name can be written as (R)-2-bromo-3-pentanone.
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Chapter 16 Solutions
Organic Chemistry
- On the next page is an LC separation of the parabens found in baby wash. Parabens are suspected in a link to breast cancer therefore an accurate way to quantitate them is desired. a. In the chromatogram, estimate k' for ethyl paraben. Clearly indicate what values you used for all the terms in your calculation. b. Is this a "good" value for a capacity factor? Explain. c. What is the resolution between n-Propyl paraben and n-Butyl paraben? Again, indicate clearly what values you used in your calculation. MAU | Methyl paraben 40 20 0 -2 Ethyl paraben n-Propyl paraben n-Butyl paraben App ID 22925 6 8 minarrow_forwardd. In Figure 4, each stationary phase shows some negative correlation between plate count and retention factor. In other words, as k' increases, N decreases. Explain this relationship between k' and N. Plate Count (N) 4000 3500 2500 2000 1500 1000 Figure 4. Column efficiency (N) vs retention factor (k') for 22 nonionizable solutes on FMS (red), PGC (black), and COZ (green). 3000 Eluent compositions (acetonitrile/water, A/W) were adjusted to obtain k' less than 15, which was achieved for most solutes as follows: FMS (30/70 A/W), PGC (60/40), COZ (80/20). Slightly different compositions were used for the most highly retained solutes. All columns were 50 mm × 4.6 mm id and packed with 5 um particles, except for COZ, which was packed with 3 um particles. All other chromatographic conditions were constant: column length 5 cm, column j.§. 4.6 mm, flow rate 2 mL/min, column temperature 40 °C, and injection volume 0.5 μL Log(k'x/K'ethylbenzene) FMS 1.5 1.0 0.5 0.0 ཐྭ ཋ ཤྩ བྷྲ ; 500 0 5 10…arrow_forwardf. Predict how the van Deemter curve in Figure 7 would change if the temperature were raised from 40 °C to 55 °C. Figure 7. van Desmter curves in reduced coordinates for four nitroalkane homologues (nitropropane, black; nitrobutane, red; nitropentane, blue; and nitrohexane, green) separated on the FMS phase. Chromatographic conditions: column dimensions 50 mm × 4.6 mm id, eluent 30/70 ACN/water, flow rates 0.2-5.0 mL/min, injection volume 0.5 and column temperature 40 °C. No corrections to the plate heights have been made to account for extracolumn dispersion. Reduced Plate Height (h) ° 20 40 60 Reduced Velocity (v) 8. (2) A water sample is analyzed for traces of benzene using headspace analysis. The sample and standard are spiked with a fixed amount of toluene as an internal standard. The following data are obtained: Ppb benzene Peak area benzene Peak area toluene 10.0 252 376 Sample 533 368 What is the concentration of benzene in the sample?arrow_forward
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- Normalized Intensity (a. u.) 0.5 1.0 A 3D-printed GC column (shown below) was created for use with "micro" gas chromatography applications. To prove its utility, it was used to separate a mixture of alkanes (C9-C18, C22, C24). For the separation shown below, the column temperature was ramped from 40 °C to 250 °C at a rate of 30 °C per minute. (a) 9 10 = 1 mm 12 13 15 22 0.0 0 100 200 300 400 Time (sec) a) What detector would you use for this analysis? Justify your selection. b) Explain how the chromatogram would change if the separation was run isothermally. c) Explain how the chromatogram would change if the temperature ramp were increased to 50 °C per minute.arrow_forwardDevise a synthesis of each compound from the indicated starting material. You may also use any organic compounds with one or two carbons and any needed inorganic reagents. a. Brarrow_forwardPlease help me with #2b & #3 using the data.arrow_forward
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- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
