What hydrocarbon with molecular formula C 4 H 10 forms only two monochlorinated products? Both products are achiral.

All right. Hi, everyone. So for this question, it's asking us which isomer with the formula C seven H 16 forms only three mono brominated products, one primary, one secondary and one tertiary. Two of these products are a chiro and one is Cairo. So here, right, the first thing that sticks out to me is the fact that we have seven carbons in total, but only three mono brominated products. So the fact that we have less products than there are carbons indicates that there's an element of symmetry to this molecule because recall that the number of mono brominated products that you get depends only on the number of non equivalent carbon hydrogen bonds. There are, right? Because if we have a molecule that has an element of symmetry to it, then some carbons may actually be equivalent and form the same exact product after bro or halogen nation. So here, right? The fact that we have to have one primary and one secondary carbon in particular indicates to me that we might need an ethos substituent or an EHO group, right? And an EHO group because it has two carbons, it would indicate that I need five carbons in my parent chain. So let me go ahead and draw that think so. So now the question becomes, where should I put my EO group? Well here, right, I'm interested in symmetry. And if I want symmetry in this molecule, I could go ahead and put my EO group on carbon three of my parent chain because now look at what you form, right? You end up with one tertiary carbon in the center and two carbon chains surrounding it. So that would justify the symmetry that we see. So now let's go ahead and take this molecule right and discuss what products it would form after mono, bro. So when we go ahead and react this molecule here, this all can with BR two in the presence of light, then we should get three distinct products because there are only three distinct carbon hydrogen bonds. Like I said before, there are three primary carbons in this molecule. But due to the element of symmetry, they would result in the same exact product in which now we have a bromine on a primary carbon. And the same is true for the secondary carbons, right? There are three of them but brominated, any of them would result in the same product. And lastly, there's only one tertiary carbon, but that would result in only one product. So here, right, only our secondary och hali is Cairo because it is the only one connected to four unique substitutes or rather it has a carbon connected to four unique substitutes. The other two are a carro. So here is going to be your final answer, right? The isomer in question is three. So pente, because due to the element of symmetry that's present in, in three ethyl pentane, you end up with less mono brominated products than there are carbons in total. So that's pretty much it. Thank you so much for watching and I hope you found this helpful.

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1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

11. Radical Reactions

Free Radical Halogenation

Organic Chemistry

11. Radical Reactions

Free Radical Halogenation

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Problem 15a

Textbook Question

What hydrocarbon with molecular formula C₄H₁₀ forms only two monochlorinated products? Both products are achiral.

Verified step by step guidance

Step 1: Begin by analyzing the molecular formula C4H10. This formula corresponds to an alkane, as it follows the general formula CnH2n+2 for saturated hydrocarbons.

Step 2: Recognize that the problem asks for a hydrocarbon that forms only two monochlorinated products. This implies that the molecule must have only two types of equivalent hydrogen atoms that can be substituted by chlorine.

Step 3: Consider the possible isomers of C4H10. There are two structural isomers: n-butane (a straight-chain alkane) and isobutane (a branched alkane). Evaluate each isomer for the number of unique hydrogen environments.

Step 4: For n-butane, there are two types of hydrogen environments: primary hydrogens (on the terminal carbons) and secondary hydrogens (on the internal carbons). Chlorination of n-butane would result in two distinct monochlorinated products, both of which are achiral.

Step 5: For isobutane, there are also two types of hydrogen environments: primary hydrogens (on the three equivalent methyl groups) and a tertiary hydrogen (on the central carbon). Chlorination of isobutane would also result in two distinct monochlorinated products, but one of them would be chiral. Therefore, the correct hydrocarbon is n-butane.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Hydrocarbons

Hydrocarbons are organic compounds consisting entirely of hydrogen and carbon atoms. They can be classified into aliphatic (alkanes, alkenes, alkynes) and aromatic hydrocarbons. The molecular formula C4H10 indicates an alkane, specifically butane, which can undergo substitution reactions, such as chlorination, to form chlorinated derivatives.

Monochlorination

Monochlorination refers to the substitution reaction where one hydrogen atom in a hydrocarbon is replaced by a chlorine atom. For alkanes, this process can yield multiple products depending on the number of unique hydrogen atoms available for substitution. In the case of C4H10, the presence of symmetrical structures leads to only two distinct monochlorinated products.

Chirality

Chirality is a property of a molecule that makes it non-superimposable on its mirror image, often due to the presence of a chiral center (a carbon atom bonded to four different groups). Achiral molecules, on the other hand, have symmetry and do not exhibit this property. The question specifies that both monochlorinated products are achiral, indicating that the substitution occurs at positions that do not create chiral centers.

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