Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 23.1, Problem 2P
Interpretation Introduction
Interpretation:
Using curved arrows to indicate the electron flow in each step, how the base catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone, is to be shown.
Concept introduction:
The steps involved in the retro-aldol reaction are i) Deprotonation by the base used ii) Elimination of the enolate ion iii) Protonation of the anion.
To show:
Using curved arrows to indicate the electron flow in each step how the base catalyzed retro-aldol reaction of 4-hydroxy-4-methyl-2-pentanone takes place to yield 2 equivalents of acetone.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Predict the major products of this organic reaction:
1. NaH (20°C)
2. CH3Br
?
Some notes:
• Draw only the major product, or products. You can draw them in any arrangement you like.
• Be sure to use wedge and dash bonds where necessary, for example to distinguish between major products that are enantiomers.
• If there are no products, just check the box under the drawing area.
No reaction.
Click and drag to start drawing a structure.
G
Cr
Predict the major products of this organic reaction:
1. LDA (-78°C)
?
2. Br
Some notes:
• Draw only the major product, or products. You can draw them in any arrangement you like.
.
• Be sure to use wedge and dash bonds where necessary, for example to distinguish between major products that are enantiomers.
• If there are no products, just check the box under the drawing area.
No reaction.
Click and drag to start drawing a structure.
X
Please draw the structures
Chapter 23 Solutions
Organic Chemistry
Ch. 23.1 - Prob. 1PCh. 23.1 - Prob. 2PCh. 23.3 - Prob. 3PCh. 23.3 - Prob. 4PCh. 23.4 - Prob. 5PCh. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7PCh. 23.5 - Prob. 8PCh. 23.6 - Prob. 9PCh. 23.6 - What product would you Expect to obtain from base...
Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
Knowledge Booster
Similar questions
- Draw the missing intermediates 1 and 2, plus the final product 3, of this synthesis: 0 1. Eto 1. Eto- 1 2 2. MeBr 2. EtBr H3O+ A 3 You can draw the three structures in any arrangement you like. Explanation Check Click and drag to start drawing a structure.arrow_forwardDraw the missing intermediate 1 and final product 2 of this synthesis: 1. MeO- H3O+ 1 2 2. PrBr Δ You can draw the two structures in any arrangement you like. Click and drag to start drawing a structure.arrow_forwardWhat is the differences between: Glyceride and phosphoglyceride Wax and Fat Soap and Fatty acid HDL and LDL cholesterol Phospho lipids and sphingosine What are the types of lipids? What are the main lipid components of membrane structures? How could lipids play important rules as signaling molecules and building units? The structure variety of lipids makes them to play significant rules in our body, conclude breifly on this statement.arrow_forward
- What is the differences between DNA and RNA for the following: - structure - function - type What is the meaning of: - replication - transcription - translation show the base pair connection(hydrogen bond) in DNA and RNAarrow_forwardWhat is the IP for a amino acid- give an example what are the types of amino acids What are the structures of proteins The N-Terminal analysis by the Edman method shows saralasin contains sarcosine at the N-terminus. Partial hydrolysis of saralasin with dilute hydrochloric acid yields the following fragments: Try-Val-His Sar-Arg-Val His-Pro-Ala Val- Tyr- Val Arg-Val-Tyr What is the structure of saralasin?arrow_forwardWhat is the IP for a amino acid- give an example what are the types of amino acids What are the structures of proteins The N-Terminal analysis by the Edman method shows saralasin contains sarcosine at the N-terminus. Partial hydrolysis of saralasin with dilute hydrochloric acid yields the following fragments: Try-Val-His Sar-Arg-Val His-Pro-Ala Val- Tyr- Val Arg-Val-Tyr What is the structure of saralasin?arrow_forward
- > aw the missing intermediates 1 and 2, plus the final product 3, of this synthesis: 1. Eto 1. EtO¯ H3O+ 1 2 2. PrBr 2. PrBr Δ You can draw the three structures in any arrangement you like. 3 Click and drag to start drawing a structure. Explanation Check 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use Privacarrow_forwardThere are various factors that affect an equilibrium. Give 3 of these factors and explain using examples andequations how an equilibrium is affected by these factors. Please remember that this is a communication question so that you are communicating your understanding of the factors that affect and equilibrium.arrow_forwardEEZE LETCHUP ID Draw the most likely conjugate base resulting from this acid-base reaction. Include all lone pairs. Ignore inorganic byproducts. Drawing く NaOCH2CH3 :0: :0: 狗arrow_forward
- Answerarrow_forward2. Provide a clear arrow-pushing mechanism for the following reactions. Do not skip proton transfers, do not combine steps, and make sure your arrows are clear enough to be interpreted without ambiguity. a. CH3 Ph OEt هد Ph CH3 Hint: the species on the left is an ynolate, which behaves a lot like an enolate.arrow_forwardb. CH3 H3C CH3 CH3 H3C an unexpected product, containing a single 9- membered ring the expected product, containing two fused rings H3C-I (H3C)2CuLi an enolatearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning