From the given compounds, the four β − hydroxy aldehyde formed by crossed aldol reaction are to be predicted. Concept introduction: Electrophiles are electron deficient species that has positive or partially positive charge. Lewis acids are electrophiles that accept electron pair. Nucleophiles are electron-rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair. Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive. Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction. Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction. Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules. A carbon-carbon bond formation occurs by aldol addition and aldol condensation reaction. Aldol reaction is preferred in basic conditions over acidic conditions as after the aldol condensation, acid catalysis promotes the reaction further. An aldol reaction takes place by acid catalysis, and direct dehydration of β − hydroxy aldol intermediate forms α , β − unsaturated product. A chemical reaction that is catalyzed by an acid is called acid catalyzed reaction. A chemical reaction that is catalyzed by a base is called base catalyzed reaction. An aldol reaction takes place in a protic solvent with a base. Dehydration of aldol addition product leads to the formation of conjugated α , β − unsaturated carbonyl compound and the overall reaction is aldol condensation. A reaction between two different carbonyl compounds known as a crossed aldol reaction. A crossed aldol reaction forms mixture of products by pairing different carbonyl reactants.

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achieve.macmillanlearning.com Canvas EA eac h Hulu YouTube G 3 methyl cyclobutanol - Google Search Ranking Phenol Acidity Course -236 - Organic Chemistry - Mac... ← Assessment Completed 10 of 22 Questions 1 + Netflix paramount plus chem hw Galdehyde reaction with grignard reagent... b My Questions | bartleby M Inbox - chenteislegit@gmail.com - Gmail Due: Fri, Jan 31 Resources Solution Penalized ? Hint Submit Answer Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag the appropriate image to the correct position in the reactions.) Route 1 Aldehyde 1 or +98 Aldehyde 2 Route 2 Q6 +100 Solved in 1 attempt Q7 +95 Solved in 2 attempts Q8 +98 Unlimited attempts possible + + Grignard 1 OH H3O+ Grignard 2 Answer Bank Q9 +90 MgBr Unlimited attempts possible CH3CH2CH2MgBr Q10 Unlimited attempts Q11 ? ? +100 in 1 attempt 2-methyl-3-hexanol CH3CH2MgBr H H о H Attempt 3

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Question

Chapter 19, Problem 34P

Interpretation Introduction

Interpretation:

From the given compounds, the four β− hydroxy aldehyde formed by crossed aldol reaction are to be predicted.

Concept introduction:

Electrophiles are electron deficient species that has positive or partially positive charge. Lewis acids are electrophiles that accept electron pair.

Nucleophiles are electron-rich species that has negative or partially negative charge. Lewis bases are nucleophiles that donate electron pair.

Free radical is an atom, molecule, or ion that has an unpaired electron, which makes it highly chemically reactive.

Substitution reaction: A reaction in which one of the hydrogen atoms of a hydrocarbon or a functional group is substituted by any other functional group is called substitution reaction.

Elimination reaction: A reaction in which two substituent groups are detached and a double bond is formed is called elimination reaction.

Addition reaction: It is the reaction in which unsaturated bonds are converted to saturated molecules by the addition of molecules.

A carbon-carbon bond formation occurs by aldol addition and aldol condensation reaction.

Aldol reaction is preferred in basic conditions over acidic conditions as after the aldol condensation, acid catalysis promotes the reaction further.

An aldol reaction takes place by acid catalysis, and direct dehydration of β− hydroxy aldol intermediate forms α,β− unsaturated product.

A chemical reaction that is catalyzed by an acid is called acid catalyzed reaction.

A chemical reaction that is catalyzed by a base is called base catalyzed reaction.

An aldol reaction takes place in a protic solvent with a base.

Dehydration of aldol addition product leads to the formation of conjugated α,β− unsaturated carbonyl compound and the overall reaction is aldol condensation.

A reaction between two different carbonyl compounds known as a crossed aldol reaction.

A crossed aldol reaction forms mixture of products by pairing different carbonyl reactants.

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achieve.macmillanlearning.com Canvas EA eac h Hulu YouTube G 3 methyl cyclobutanol - Google Search Ranking Phenol Acidity Course -236 - Organic Chemistry - Mac... ← Assessment Completed 10 of 22 Questions 1 + Netflix paramount plus chem hw Galdehyde reaction with grignard reagent... b My Questions | bartleby M Inbox - chenteislegit@gmail.com - Gmail Due: Fri, Jan 31 Resources Solution Penalized ? Hint Submit Answer Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag the appropriate image to the correct position in the reactions.) Route 1 Aldehyde 1 or +98 Aldehyde 2 Route 2 Q6 +100 Solved in 1 attempt Q7 +95 Solved in 2 attempts Q8 +98 Unlimited attempts possible + + Grignard 1 OH H3O+ Grignard 2 Answer Bank Q9 +90 MgBr Unlimited attempts possible CH3CH2CH2MgBr Q10 Unlimited attempts Q11 ? ? +100 in 1 attempt 2-methyl-3-hexanol CH3CH2MgBr H H о H Attempt 3

2) (4 pt) After the reaction was completed, the student collected the following data. Crude product data is the data collected after the reaction is finished, but before the product is purified. "Pure" product data is the data collected after attempted purification using recrystallization. Student B's data: Crude product data "Pure" product data after recrystallization Crude mass: 0.93 g grey solid Crude mp: 96-106 °C Crude % yield: Pure mass: 0.39 g white solid Pure mp: 111-113 °C Pure % yield: a) Calculate the crude and pure percent yields for the student's reaction. b) Summarize what is indicated by the crude and pure melting points.

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