Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 18, Problem 18.37SP

Draw structures of the following derivatives.

  1. a. the 2,4-dinitrophenylhydrazone of benzaldehyde
  2. b. the semicarbazone of cyclobutanone
  3. c. cyclopropanone oxime
  4. d. the ethylene acetal of hexan-3-one
  5. e. acetaldehyde dimethyl acetal
  6. f. the methyl hemiacetal of formaldehyde
  7. g. the (E) isomer of the ethyl imine of propiophenone
  8. h. the hemiacetal form of 5-hydroxypentanal

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 1.

Explanation of Solution

The given derivative is 2,4-dinitrophenylhydrazone of benzaldehyde.

The 2,4-dinitrophenylhydrazine is treated with benzaldehyde to form a 2,4-dinitrophenylhydrazone derivative.

The structure of 2,4-dinitrophenylhydrazone of benzaldehyde is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  1

Figure 1

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 2.

Explanation of Solution

The given derivative is semicarbazone of cyclobutanone.

The cyclobutanone is treated with semicarbazide to form a semicarbazone derivative.

The structure of semicarbazone of cyclobutanone is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  2

Figure 2

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 3.

Explanation of Solution

The given derivative is cyclopropanone oxime.

The cyclopropanone is treated with hydroxylamine to form an oxime.

The structure of cyclopropanone oxime is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  3

Figure 3

(d)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 4.

Explanation of Solution

The given derivative is ethylene acetal of hexan-3-one.

The ethylene glycol is treated with hexan-3-one to form ethylene acetal of hexan-3-one.

The structure of ethylene acetal of hexan-3-one is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  4

Figure 4

(e)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 5.

Explanation of Solution

The given derivative is acetaldehyde dimethyl acetal.

The acetaldehyde is treated with two moles of ethyl alcohol to form acetaldehyde dimethyl acetal.

The structure of acetaldehyde dimethyl acetal is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  5

Figure 5

(f)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 6.

Explanation of Solution

The given derivative is methyl hemiacetal of formaldehyde.

The structure of hemiacetal of formaldehyde is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  6

Figure 6

(g)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 7.

Explanation of Solution

The given derivative is (E)-isomer of the ethyl imine of propiophenone.

The propiophenone is treated with ethyl amine to form an ethyl imine derivative.

The structure of (E)-isomer of the ethyl imine of propiophenone is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  7

Figure 7

(h)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The structure of the given derivative is to be drawn.

Concept introduction:

Ketones and aldehydes show different types of reactions which results to form many different products. The nucleophilic addition reactions are the common reactions, which form products like imines, diols, alcohols, cyanohydrins, and alkenes.

Answer to Problem 18.37SP

The structure of the given derivative is shown in Figure 8.

Explanation of Solution

The given derivative is hemiacetal of 5-hydroxypentanal.

The structure of hemiacetal of 5-hydroxypentanal is given as,

Organic Chemistry (9th Edition), Chapter 18, Problem 18.37SP , additional homework tip  8

Figure 8

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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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