Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
Question
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Chapter 18.10, Problem 18.10P

(a)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be predicted.

Concept introduction: The reaction of acid chloride with strong reducing agent such as LiAlH4 to give product primary alcohol.

Acid chlorides are reactive derivative of carboxylic acids in which acidic hydroxy group are replaced by a chlorine atom.

(b)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be predicted.

Concept introduction: The reaction of acid chloride with mild reducing agent LiAl(OtBu)3 to give the aldehyde as a product.

Acid chlorides are reactive derivative of carboxylic acids in which acidic hydroxy group are replaced by a chlorine atom

(c)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be predicted.

Concept introduction: The reaction of acid chloride with lithium dialkylcuprate to give the product as ketone.

Acid chlorides are reactive derivative of carboxylic acids in which acidic hydroxy group are replaced by a chlorine atom

(d)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be predicted.

Concept introduction: The reaction of acid chloride with excess organolithium reagent then followed by the hydrolysis to give product as tertiary alcohol.

Acid chlorides are reactive derivative of carboxylic acids in which acidic hydroxy group are replaced by a chlorine atom

(e)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be predicted.

Concept introduction: The reaction of ester with diisobutylaluminium hydride at dry ice temperature to give aldehyde as a product.

Cold diisobutylaluminium hydride usually does not reduce the aldehydes further.

(f)

Interpretation Introduction

To determine: The product of the given reaction.

Interpretation: The product of the given reaction is to be predicted.

Concept introduction: The reaction of ester with diisobutylaluminium hydride at dry ice temperature to give aldehyde as a product.

Cold diisobutylaluminium hydride usually does not reduce the aldehydes further.

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Chapter 18 Solutions

Organic Chemistry (9th Edition)

Ch. 18.11 - Show how you would accomplish the following...Ch. 18.11 - Prob. 18.12PCh. 18.12 - Propose mechanisms for a. the acid-catalyzed...Ch. 18.12 - Rank the following compounds in order of...Ch. 18.13 - Prob. 18.15PCh. 18.13 - Show how you would accomplish the following...Ch. 18.14 - Prob. 18.17PCh. 18.14 - Prob. 18.18PCh. 18.14 - Prob. 18.19PCh. 18.14 - Prob. 18.20PCh. 18.15 - 2,4-Dinitrophenylhydrazine is frequently used for...Ch. 18.15 - Prob. 18.22PCh. 18.15 - Prob. 18.23PCh. 18.16 - Prob. 18.24PCh. 18.16 - Prob. 18.25PCh. 18.16 - Show what alcohols and carbonyl compounds give the...Ch. 18.16 - In the mechanism for acetal hydrolysis shown, the...Ch. 18.16 - Prob. 18.28PCh. 18.17 - Show how you would accomplish the following...Ch. 18.18 - Prob. 18.30PCh. 18.18 - Prob. 18.31PCh. 18.18 - Prob. 18.32PCh. 18.18 - Show how Wittig reactions might be used to...Ch. 18.19 - Predict the major products of the following...Ch. 18.20C - Prob. 18.35PCh. 18.20C - Predict the major products of the following...Ch. 18 - Draw structures of the following derivatives. a....Ch. 18 - Prob. 18.38SPCh. 18 - Predict the major products of the following...Ch. 18 - Rank the following carbonyl compounds in order of...Ch. 18 - Acetals can serve as protecting groups for...Ch. 18 - Sketch the expected proton NMR spectrum of...Ch. 18 - A compound of formula C6H10O2 shows only two...Ch. 18 - The proton NMR spectrum of a compound of formula...Ch. 18 - The following compounds undergo McLafferty...Ch. 18 - An unknown compound gives a molecular ion of m/z...Ch. 18 - Show how you would accomplish the following...Ch. 18 - Prob. 18.48SPCh. 18 - Prob. 18.49SPCh. 18 - Propose mechanisms for the following reactions.Ch. 18 - Show how you would accomplish the following...Ch. 18 - Show how you would synthesize the following...Ch. 18 - Predict the products formed when cyclohexanone...Ch. 18 - Predict the products formed when...Ch. 18 - Show how you would synthesize octan-2-one from...Ch. 18 - Prob. 18.56SPCh. 18 - Both NaBH4 and NaBD4 are commercially available,...Ch. 18 - When LiAIH4 reduces 3-methylcyclopentanone, the...Ch. 18 - Prob. 18.59SPCh. 18 - Show how you would accomplish the following...Ch. 18 - There are three dioxane isomers 1,2-dioxane,...Ch. 18 - Two structures for the sugar glucose are shown on...Ch. 18 - Prob. 18.63SPCh. 18 - Prob. 18.64SPCh. 18 - Prob. 18.65SPCh. 18 - Prob. 18.66SPCh. 18 - Within each set of structures, indicate which will...Ch. 18 - Prob. 18.68SPCh. 18 - Prob. 18.69SPCh. 18 - Prob. 18.70SPCh. 18 - The UV spectrum of an unknown compound shows...Ch. 18 - a. Simple aminoacetals hydrolyze quickly and...Ch. 18 - The mass spectrum of unknown compound A shows a...Ch. 18 - Prob. 18.74SPCh. 18 - Prob. 18.75SPCh. 18 - Prob. 18.76SPCh. 18 - Prob. 18.77SP
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