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

Previous problemNext problem

5:34 minutes

Problem 51a-d

Textbook Question

Propose structures for intermediates and products (A) through (D).

Verified step by step guidance

Step 1: Begin with 1-bromobutane. React it with KOH and H2O to perform an elimination reaction, forming but-1-ene (A). This reaction removes the bromine atom and introduces a double bond.

Step 2: Treat but-1-ene (A) with sodium metal (Na). This reaction generates a sodium alkoxide intermediate (B), which is highly reactive.

Step 3: React intermediate (B) with ethyl bromide (CH3CH2Br) to perform an alkylation reaction, forming pentane (C). This step involves the nucleophilic substitution of the bromine atom in ethyl bromide.

Step 4: React 1-bromobutane with magnesium in ether to form a Grignard reagent (D). This reagent is highly nucleophilic and can react with aldehydes or ketones.

Step 5: Use the Grignard reagent (D) to react with CH3(CH2)3CHO (butanal) in the presence of H3O+ to form a secondary alcohol (E). This reaction involves nucleophilic addition of the Grignard reagent to the carbonyl group of butanal.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above

Video duration:

Play a video:

Was this helpful?

Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. A clear grasp of mechanisms helps predict the structure of intermediates and products based on the starting materials and conditions.

Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups is essential for predicting how compounds will behave in reactions, as they dictate the reactivity and properties of the organic molecules involved in the proposed structures.

Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is important for understanding isomerism, including enantiomers and diastereomers, which can have vastly different properties. In proposing structures for intermediates and products, considering stereochemistry ensures accurate representation of the molecules' three-dimensional shapes.

Watch next

Master Intro to Predict the Product with a bite sized video explanation from Johnny

Start learning

Related Videos

Related Practice

Textbook Question

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(d) cyclopentyl propyl ketone

Textbook Question

Show how you would accomplish the following synthetic

conversions by adding an organolithium reagent to an acid.

Textbook Question

Predict the products of the following reactions:

(c)

(d)

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one

Textbook Question

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

f. 1-(phenylmethyl)cyclohexanol

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(a)

Textbook Question

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(b)

Textbook Question

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(p)

Show more practices

Download the Mobile app

Privacy

Do not sell my personal information

Accessibility

Patent notice

Sitemap