Table of contents

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

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

Organic Chemistry

13. Alcohols and Carbonyl Compounds

Organometallic Cumulative Practice

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5:15 minutes

Problem 13a

Textbook Question

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.
a. 3-phenylprop-1-ene

Verified step by step guidance

Step 1: Begin with bromobenzene (C6H5Br) as the starting material. Perform a Grignard reaction by reacting bromobenzene with magnesium (Mg) in dry ether to form phenylmagnesium bromide (C6H5MgBr). This is a key organometallic intermediate.

Step 2: Prepare propenal (CH2=CH-CHO), which is an alkenyl compound with three carbon atoms. This can be synthesized separately if not readily available.

Step 3: Perform a nucleophilic addition reaction between phenylmagnesium bromide (C6H5MgBr) and propenal (CH2=CH-CHO). The Grignard reagent will attack the carbonyl carbon of propenal, forming an intermediate alcohol.

Step 4: Dehydrate the intermediate alcohol to form 3-phenylprop-1-ene (C6H5-CH=CH-CH2). This can be achieved using an acid catalyst, such as concentrated sulfuric acid (H2SO4), to remove water and form the double bond.

Step 5: Purify the product using distillation or another appropriate method to isolate 3-phenylprop-1-ene. Confirm the structure using spectroscopic techniques such as NMR or IR.

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Key Concepts

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

Electrophilic Aromatic Substitution

Electrophilic aromatic substitution (EAS) is a fundamental reaction in organic chemistry where an electrophile replaces a hydrogen atom on an aromatic ring. In the context of synthesizing 3-phenylprop-1-ene from bromobenzene, EAS can be used to introduce a propyl group onto the benzene ring, forming a substituted aromatic compound that can further undergo elimination to yield the desired alkene.

Alkylation Reactions

Alkylation reactions involve the introduction of an alkyl group into a molecule, often through nucleophilic substitution or EAS. In this synthesis, alkyl halides can react with bromobenzene to form a new carbon-carbon bond, which is crucial for building the propyl chain needed for 3-phenylprop-1-ene. Understanding the reactivity of alkyl halides is essential for selecting the appropriate reaction conditions.

Elimination Reactions

Elimination reactions are processes where elements of the starting material are removed, resulting in the formation of a double bond. In synthesizing 3-phenylprop-1-ene, after the alkylation step, an elimination reaction can be performed to remove a leaving group and generate the alkene. This step is vital for achieving the final product with the desired double bond configuration.

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Textbook Question

Show how this 1° alcohol can be made from the following:

(b) formaldehyde

Textbook Question

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(a)

Textbook Question

What organocuprate reagent would you use for the following substitutions?

(a)

(b)

Textbook Question

What products would you expect from the following reactions?

(a)

(b)

Textbook Question

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.

b. 5-methylhex-2-ene