Core Organic Chemistry Graded Coursework

Core Organic Chemistry Graded Coursework

Ac 1.1

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IUPAC system of the nomenclature established the international standard of naming for the flexibility of the compounds. 

 Fundamental principles 

The nomenclature is completely based on the longest chain of carbons connected with the single bonds; it can be a continuous chain or maybe a ring. Other groups except for the carbon and hydrogen groups are identified by the prefixes and suffixes. 

1.

1. a) C₃H₈

IUPAC name of this molecule is n-propane, Dimethyl methane, or Propyl hydride. This molecule belongs to the Alkane group, which is following the formula of CnH2n+2.

1. b) CH₃CH₂CH₂CH₂CH₃

In this molecule, there are 5 Carbon atoms connected with the single bonds. The suffix is here is “ane.” That is the reason the name of the compound is pentane. It is known as the “n-pentane.”

1. c) CH₃CH (CH₃) CH₂CH₂CH₂CH₃

In this compound there are 6 carbons are present in the linear structure and the second carbon methyl group is associated. That is the reason the name of the compound is started with the position of the methyl group and the IUPAC name of this compound is “2-methylhexane.”

1. d) CH₃CH₂CH₂Br

The compound is the “bromoderivative of alkanes.” The name of the compound is “Alkyl bromide or bromoalkane.” According to the IUPAC rules by the analysis of the position of the bromine group the name of the compound is 1-bromopropane.

1. e) CH₂CH₂

The compound is representing the hydrocarbon group. The IUPAC name of the compound is “Ethene.” It is the simplest form “alkene.”

1. f) CH₃CH=CHCH₃

This compound is showing the fact of the symmetrical structure in both says of the double bond. In a compound there are 4 carbon atoms are present. Here the prefix is “But.” There is a double bond between the 2 and 3 carbon groups. That is the reason the suffix is “ene.” The name of the compound is “2-butene.”

1. g) CH=CH CH₂CH₂CH₂ CH₂

Cyclohexene represents the group of hydrocarbons. This is mainly produced from the “hydrogenation of the benzene.” Here the carbon number is 6, which is the reason the prefix is “hex.”

1. h) C₂H₅OH

As per the IUPAC nomenclature the root word is here eth (here 2 carbon groups are present) and the primary suffix is ane and the secondary suffix is ol. Overall, the name of the molecule as per the IUPAC rule is “ethanol.”

1. I) CH₃CH₂CH₂CH₂CH₂CHOHCH₃

In this compound as a functional group, the “enol” group is associated with the carbon number 2 and here seven carbon atoms are present that is the reason the prefix is here is “hepta.” Overall, the name of the compound is “2-heptanol.”

1. J) CH₃CH₂COOH

The compound group containing the functional group is “Carboxylic acid.” The longest chain is here three carbon chains. The suffix is here “oic acid.” Here the number of the carbon is three that is the reason the prefix is “propane." Overall, the name of the compound is “Propanoic Acid.”

1. K) CH₃CH₂CH₂CHO

In this compound, the functional group is "Aldehyde group.” Here four carbon atoms are present which is the reason the hydrocarbon is named the “butane.” The IUPAC name of the compound is “butanal.”

1. L) CH₃-CO-CH₃

In this compound, the “Ketone” group is present as the functional group. This is one type of Hydrocarbon derivative. In this compound, the functional group is associated with the carbon number 2 which is the reason its name is 2-propanone. The general name of the compound is Acetone.

1. m) CH₃CH₂-O-CO-CH₃

The compound is the representation of the R-COO-R ester group. The suffix of the ester group is “-oate.” The full name of this compound as per the rule of the IUPAC is “ethyl ethanoate.”

AC.2 a)

Figure 1: 3-ethylpentane

(Source: Estopiñá-Durán et al. 2020)

b)

Figure 2: 3-Chlorobutan-2-ol

(Source: Li et al. 2020)

1. C)

Figure 3: 1-Bromo-2, 2-dimethyl propane

(Source: Li et al. 2020)

3. a) Structural isomers

The concept of Structural isomers is completely based on the arrangement of the atoms. In this particular type of compound, the arrangement of the atoms is different from one another that have similar molecular formulas (Meng et al. 2018). Different types of connectives are observed in this type of compound. Different bonding can also be present in different arrangements.

b)

1. i) Chain Isomerism

In this particular type of isomerism, differentiation is observed between two or more compounds that have a similar molecular formula but the arrangement of the carbon atoms  are different in the straight or branched chains.

Example: The formula of a compound is C₅H₁₂, which can show the chain isomerism because there are three compounds present "n-pentane, 2-methyl butane and 2, 2 dimethyl-propane.”

Figure 4: Chain Isomerism

(Source: Meng et al. 2018)

1. ii) Position Isomerism

Positional isomerism or the position isomerism shows the same functional groups but the positions of those functional groups are different from each other.

Example: Suppose the chemical formula is C₆H₄Br₂ and there are three isomers are present in this same formula and they are “1,2-dibromobenzene, 1,3-dibromobenzene and 1,4 dibromobenzene.” Here the functional group is the “dibromo group”  but their positions are different.

Figure 5: Positional isomerism

(Source: Li et al. 2020)

iii) Functional isomerism

Functional group isomerism, also called functional isomerism, which is completely based on the atoms, creates different functional groups. Different functional groups are present in these isomers.

Example: The molecular formula is dimethyl ether, and ethanol or ethyl alcohol, which contains different functional groups.

1. C)
2. I) the two compounds of the chemical formula C4H10 that shows the isomeric compounds are as follows:

1) “n-butane”

Figure 6: “n-butane”

(Source: Meng et al. 2018)

2) “Isobutane”

Figure 7: “Isobutane”

(Source: Meng et al. 2018)

1. II) Structural Isomer of C₄H₁₀O
   • “n-butanol”

Figure 8: “n-Butanol”

(Source: Motsch et al. 2018)

• “Sec-Butanol”

Figure 9: “Sec-Butanol”

(Source: Motsch et al. 2018)

• “Tert-Butanol”

Figure 10: “tert- Butanol”

(Source: Zhang et al. 2022)

• “Isobutanol”

Figure 11: “Iso-butanol”

(Source: Zhang et al. 2022)

1. d) Two functional group isomers with formula C₃H₆O

1.1) “Prop-2-en-1-ol”

Figure 12: “Prop-2-en-1-ol”

(Source: Rana et al. 2021)

1.2) “Methoxyethene”

Figure 13: “Methoxyethene”

(Source: Rana et al. 2021)

4)

1. a) “Stereoisomers”

Stereoisomer is part of isomers, which have the same type of composition but they are completely different from each other by their orientation. They show the same molecular formulaand differ in their atomic structure in the 3d space.

1. b) “But-2-ene” represents the two different groups of the alkene carbon. E and Z isomers of this compound show the differences between the positions of the substituents, which are located on the double-bonded atoms. These two isomers are named are as follows:

1) “Cis-but-2-ene” (Z-isomer)

Figure 14:“Cis-but-2-ene”

(Source: Motsch et al. 2018)

2) “trans-but-2-ene”( E isomer)

Figure 15: “trans-but-2-ene”

(Source: An and Xiao, 2020)

1. c) Stereoisomers of “3, 4-dimethylhex-3-ene”

1.1) “E isomer of 3,4-dimethylhex-3-ene”

Figure 16: “E isomer of 3,4-dimethylhex-3-ene”

(Source: An and Xiao, 2020)

1.2) “Z-isomer of 3, 4-dimethylhex-3-ene”

Figure 17: “Z-isomer of 3,4-dimethylhex-3-ene”

(Source: Guérinot, A. and Cossy, J., 2020)

AC 2.1

• a) Complete combustion

In the presence of excess Oxygen, alkanes are burnt through complete combustion. In this particular situation, the alkane is heated with the help of this oxygen. Heat energy is released.

Example:

 C₃H₈ + 5O₂ – 3CO₂ + 4H₂O

1. b) Incomplete combustion

Incomplete combustion occurs oxygen supply is very low or poor. Carbon monoxide and carbon are produced instead of the carbon dioxide. Water is still produced in this type of combustion.

Example: C₃H₈ +2O₂-3C + 4H₂O

1. b)
2. Complete combustion of pentane

C₅H₁₂ + 8O₂- 6H₂O + 5CO₂

1. Incomplete Combustion of Pentane

C₅H₁₂ + 6O₂- 4CO +CO₂+6H₂O

• Complete Combustion of Heptane

 C₇H₁₆ + O2- CO₂+H₂O

1. Incomplete combustion of Heptane

C₇H₁₄ + 9O₂-5CO₂+ CO+ C+ 7H₂O

1. C)

Incomplete combustion of the alkenes air and the oxygen is poor. Water is still produced after this reaction but in this type of the chemical reaction Carbon monoxide and carbon are produced. The gas “Carbon monoxide” is one type of the poisonous gas, which is harmful for the humans, that is the reason complete combustion is preferred over incomplete combustion.

1. d) Impact of burning Fossils

The combustion of fossil fuels gives harmful compounds like sulfur dioxide and nitrogen oxides. This type of pollution mix with the water, oxygen, and other chemicals in the atmosphere, which is generally creates acidic pollutants (Li et al. 2020). This is known as air pollution. The increase in the burning of fossil fuels helps in the growth of the temperature, which put a negative effect on society. A huge amount of fossil fuel use is also responsible for the improvement of Global warming. The rise in the sea level, air pollution, and release of toxic gases are some of the n negative impacts on the environment. 

These problems can be mitigated by reducing the use of fossil fuels. The industry should focus on the complete combustion of fossil fuels because incomplete combustion creates toxic gases like carbon monoxide. That is the reason the reduction of the use of fossil fuels in vehicles and other equipment will ultimately help in the reduction of pollution.

2.

1. a) Photochemical reaction represents a special type of chemical reactions, which is started after the absorption of the energy, and this energy is absorbed from the light. This type of chemical reaction includes “Photo-induced rearrangements and isomerization.”
2. b) In the presence of the UV light especially in the presence of the sunlight, the mixture of the methane and the chlorine creates the substitution reaction as result chloromethane is produced.

Reaction:

CH₄ + Cl₂- CH₃CL +HCL

The three steps of this photochemical reaction are as follows:

1. Initiation

In this, step-free radicals are created with the help of ultraviolet light.

2. Propagation

In this step, the chlorine molecule abstracts the hydrogen from the methane.

3. Termination

In this step, radicals are produced in the mechanism, which ultimately produces the sigma bond.

1. c) Chemical reactions:

Figure 18: “Photochemical reaction and production of Chloromethane.”

(Source: Guérinot, A. and Cossy, J., 2020)

AC 3.1

1. a) The alkenes are generally identified as the unsaturated hydrocarbons because “two atoms can join onto half of the carbon = carbon double bond when it opens up.” Carbon to carbon double bond is observed in this type of the molecule (Motsch et al.2018).

b)

Figure 19: Carbon-Carbon double bond formation

 (Source: Guérinot and Cossy, 2020)

1. C) Ethene generally reacts with the hydrogenbromide and this reaction occurs in the presence of the nickel catalysts. The double bond breaks and a hydrogen atom end by the attachment with a carbon molecule and the bromine atom attaches with the other carbon atom. This type of reaction is representing the “Electrophile addition reaction” (Guérinot and Cossy, 2020).

Reaction:

CH₂=CH₂+ HBr-CH₃CH₂Br

Diagram

Figure 20: Electrophilic addition reaction

(Source: Bartoszewicz et al. 2019)

2. Hydrogen bromide reacts with the propane and produces “1-bromopropane and 2-bromopropane” but in this reaction electrophile attacks the double bond for the formation of 1⁰ and 2⁰“Secondarycarbocation” are more stable than the primary one which makes the “2- bromopropane” major product in this reaction (Bartoszewicz et al. 2019).
3. The reaction is between the “hex-1 one” and As a result the alkene will be converted into the brown bromine water is colorless water because the bromine reacts with the carbon-carbon double bonds. As a result, the hexane reacts with the bromine more than hexane. That is the reason the bromine test is done for the identification of the alkene group (Hao et al. 2020).

1. A) Addition polymerization

This is one type of chain reaction, the monomer attaches to the polymer with the growing polymer. Loss of other atoms does not occur in this reaction.

1. B)

Figure 21: “Additional polymerization chloroethene monomers”

(Source: Meng et al. 2018)

Ac 4.1

1.1) Primary alcohol

Ethanol (C₂H₆O)

Figure 21: “Ethanol”

(Source: Huang et al. 2018)

1.2) Secondary alcohol

Sec-butyl alcohol (CH₃CH₂CHOCH₃)

Figure 22: “Sec-butyl alcohol”

(Source: Hao et al. 2020)

1.3) Tertiary alcohol

Tert-butyl alcohol (CH₃)₃COH

Figure 23: “Tert-butyl alcohol”

(Source: Motsch et al. 2018)

b)

Figure 24: “Butan-1-ol”

(Source: Bartoszewicz et al. 2019)

1. ii) Botanic acid can be obtained by the oxidation of butane-1-ol and the reagents which are used for this reaction is Chromium (VI) for the oxidation purpose and the other reagents are chromic acid (H₂CrO₄), Potassium dichromate (K₂Cr₂O₇) and Chromic anhydride (CrO₃).

iii) Butane has the polar O-H bond which shows the intermolecular h-bonding as a is next to impossible due to the absence of a polar bond.

Figure 25: “Butan-1-ol to butanal”

(Source: An and Xiao, 2020)

Formulae of butanal C₄H₈O. It belongs to the homologous series of butane.

iv)

Figure 26: “Tertbutanol that does notoxidize”

(Source: Jana et al. 2020)

2. A dehydration reaction involves the loss of the water from the reacting molecule or the ions. Propane -1- ol to the formation of the propane can niot be done generally from the propane-2 – ol will produce propane (Estopiñá-Duránet al. 2021).

1. The possible two components that are which re produced after the heating of 2-methylbutan-2-ol with concentrated sulphuric acid are 1) 2 methyl-2 butene and 2) 2 methylbut-1-ene.

3. Dehydration of the alcohol Provides different kinds of monomers like alkenes, which is the starting product of the most of the common polymers. In the polythene, the starting monomer is ethane, which is generally produced by the dehydration of ethanol (Rana et al. 2021).

4.

1. a) “Nucleophile substitution reaction” represents the class of reactions, which creates an elctron rich nucleophile attacks different positively charged electrophile for the replacement of the leaving group.

“Substitution reaction” represents a particular chemical reactions in which an atom, ion or a group of atoms are replaced by the another atom, ion or group.

b)

Figure 27: “Bromoethane to ethanol” SN₂ Mechanism

(Source: Guérinot, A. and Cossy, J., 2020)

1. C) The reaction between the primary alcohol and the secondary alcohol in the presence of the HCL gas, which is acidic, the formation of haloalkanes is done. The application of the anhydrous agent is also needed for the completion of the reaction (Anet al. 2020). ZnCl2 is acts as catalyst in this reaction. In other words, the interaction of the phosphoric acid with sodium iodide with the interaction of iodoalkane helps in the formation of haloalkanes (hydrogen iodide) with the interaction of alcohol.

Reference

An, X.D. and Xiao, J., 2020. Fluorinated alcohols: Magic reaction medium and promoters for organic synthesis. The Chemical Record, 20(2), pp.142-161.

Bartoszewicz, A., Matier, C.D. and Fu, G.C., 2019.Enantioconvergentalkylations of amines by alkyl electrophiles: copper-catalyzed nucleophilic substitutions of racemic α-halolactams by indoles. Journal of the American Chemical Society, 141(37), pp.14864-14869.

Estopiñá-Durán, S., Mclean, E.B., Donnelly, L.J., Hockin, B.M. and Taylor, J.E., 2020.Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols. Organic letters, 22(19), pp.7547-7551

Guérinot, A. and Cossy, J., 2020. Cobalt-catalyzed cross-couplings between alkyl halides and Grignard Reagents. Accounts of Chemical Research, 53(7), pp.1351-1363.

Hao, Y.J., Gong, Y., Zhou, Y., Zhou, J. and Yu, J.S., 2020.Construction of β-Quaternary α, α-Difluoroketones via Catalytic Nucleophilic Substitution of Tertiary Alcohols with Difluoroenoxysilanes. Organic Letters, 22(21), pp.8516-8521.

Huang, H., Yuan, H., Janssen, K.P., Solis-Fernandez, G., Wang, Y., Tan, C.Y., Jonckheere, D., Debroye, E., Long, J., Hendrix, J. and Hofkens, J., 2018.Efficient and selective photocatalytic oxidation of benzylic alcohols with hybrid organic–inorganic perovskite materials. ACS Energy Letters, 3(4), pp.755-759.

Jana, S., Yang, Z., Li, F., Empel, C., Ho, J. and Koenigs, R.M., 2020.Photoinduced Proton?Transfer Reactions for Mild O?H Functionalization of Unreactive Alcohols. AngewandteChemie International Edition, 59(14), pp.5562-5566.

Li, J., Kong, M., Qiao, B., Lee, R., Zhao, X. and Jiang, Z., 2018.Formal enantioconvergent substitution of alkyl halides via catalytic asymmetric photoredox radical coupling. Nature communications, 9(1), pp.1-9.

Li, Y., Yang, Y., Xin, J. and Tang, P., 2020. Nucleophilictrifluoromethoxylation of alkyl halides without silver. Nature communications, 11(1), pp.1-7.

Meng, S.S., Wang, Q., Huang, G.B., Lin, L.R., Zhao, J.L. and Chan, A.S., 2018. B (C 6 F 5) 3 catalyzed direct nucleophilic substitution of benzylic alcohols: an effective method of constructing C–O, C–S and C–C bonds from benzylic alcohols. RSC Advances, 8(54), pp.30946-30949.

Motsch, S., Schütz, C. and Huy, P.H., 2018.Systematic evaluation of sulfoxides as catalysts in nucleophilic substitutions of alcohols. European Journal of Organic Chemistry, 2018(33), pp.4541-4547.

Rana, J., Sahoo, S.T. and Daw, P., 2021. Homogeneous first-row transition metal catalyst for sustainable hydrogen production and organic transformation from methanol, formic acid, and bio-alcohols. Tetrahedron, 99, p.132473.

Zhang, W., Lu, L., Zhang, W., Wang, Y., Ware, S.D., Mondragon, J., Rein, J., Strotman, N., Lehnherr, D., See, K.A. and Lin, S., 2022. Electrochemically driven cross-electrophile coupling of alkyl halides. Nature, 604(7905), pp.292-297.