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Workbook for Organic Chemistry : Supplemental Problems and Solutions

Jerry Jenkins

Chapter 19

CARBONYL CONDENSATION REACTIONS - all with Video Answers

Educators

Section 1

Reactions

Problem 1

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
benzaldehyde + acetophenone Figure can't copy

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Problem 2

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy

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Problem 3

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy

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Problem 4

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy

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Problem 5

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
dimethyl heptanedioate $\xrightarrow[\text { 2. } \mathrm{H}_3 \mathrm{O}^{\oplus}, \Delta]{\text { 1. }{ }^{\ominus} \mathrm{OMe}} \mathrm{CO}_2+$

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Problem 6

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $\xrightarrow[\text { (conj. add'n + retro-aldol) }]{{ }^{\ominus} \mathrm{OH}, \mathrm{ROH}}$

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Problem 7

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $\xrightarrow{{ }^{\ominus} \mathrm{OH}}$

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Problem 8

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
propionaldehyde $\xrightarrow[\text { 2. } \mathrm{H}_3 \mathrm{O}^{\oplus}, \Delta(\text { Darzen's cond. })]{\text { 1. } \mathrm{BrCH}_2 \mathrm{CO}_2 \mathrm{Me}, \iota-\mathrm{BuO}^{\ominus}}$

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Problem 9

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy + propionic anhydride $\xrightarrow[2 . \text { acid (Perkin cond.) }]{1 . \text { base }}$

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Problem 10

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy + ethyl vinyl ketone $\xrightarrow{\text { base }}$ Figure can't copy

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Problem 11

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
benzaldehyde $+\mathrm{CH}_3 \mathrm{NO}_2 \xrightarrow{{ }^{\ominus} \mathrm{OH}}$

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Problem 12

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $\xrightarrow{{ }^{\ominus} \mathrm{OMe}, \mathrm{MeOH} \text { (retro-Claisen) }}$

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06:24

Problem 13

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
cyclopentanone $\xrightarrow[\text { 2. } \mathrm{NH}_2 \mathrm{NHPh}]{\text { 1. } \mathrm{NaOEt} / \mathrm{EtOH}\left(-\mathrm{H}_2 \mathrm{O}\right)}$

Anatole Borisov
Anatole Borisov
Numerade Educator

Problem 14

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $\mathrm{CO}_2+\mathrm{C}_5 \mathrm{H}_6 \mathrm{O}$

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03:50

Problem 15

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
acetone $\xrightarrow[(\text { aldol })]{{ }^{\ominus} \mathrm{OH}} \mathrm{C}_6 \mathrm{H}_{10} \mathrm{O} ~ \xrightarrow[\text { 2. } \mathrm{H}_3 \mathrm{O}^{\oplus}, \Delta]{\text { 1. } \mathrm{CH}_2\left(\mathrm{CO}_2 \mathrm{Me}\right)_2,{ }^{\ominus} \mathrm{OMe}}$ $\mathrm{C}_8 \mathrm{H}_{12} \mathrm{O}_2$

Zubair Abdulla
Zubair Abdulla
Numerade Educator

Problem 16

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy + 3-pentanone $\xrightarrow{{ }^{\ominus} \mathrm{OH}\left(-\mathrm{H}_2 \mathrm{O}\right)}$

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Problem 17

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy

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Problem 18

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy

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03:51

Problem 19

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
acetaldehyde $+($ XS $)$ formaldehyde $\xrightarrow{{ }^{\ominus} \mathrm{OH}}$

Mystique Till
Mystique Till
Numerade Educator

Problem 20

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $\xrightarrow{\mathrm{PhCHO}, \mathrm{H}^{\oplus}}$

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Problem 21

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $+\mathrm{CH}_2\left(\mathrm{CO}_2 \mathrm{Et}\right)_2 \xrightarrow[\text { 1. base }]{\text { 2. } \mathrm{H}^{\oplus}}$

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Problem 22

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy +Figure can't copy $\xrightarrow{\mathrm{KOH}}$

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Problem 23

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
A reaction in the biosynthesis of the amino acid leucine:
Figure can't copy

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Problem 24

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Trans-resveratrol, isolable from red wine, has been implicated as a cardioprotective and can be synthesized as follows:
Figure can't copy

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Problem 25

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy

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Problem 26

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Forward and retro-aldol-like reactions that occur in plants:
Figure can't copy

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Problem 27

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Figure can't copy $\xrightarrow[\text { (Robinson annulation) }]{{ }^{\ominus} \mathrm{OEt} / \mathrm{EtOH}}$

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06:28

Problem 28

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
The biosynthesis of glucose involves aldolase, an enzyme that catalyzes both forward and retro-aldol reactions. The forward process illustrates a mixed aldol wherein the enzyme initially binds with promoting its tautomerization and subsequent reaction with $\underline{\mathbf{B}}$ to form a ketohexose:
Figure can't copy

Lara Gossage
Lara Gossage
Numerade Educator

Problem 29

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
The Krebs Cycle begins with an aldol-like condensation of a thioester (acetyl coenzyme A) with oxaloacetate, followed by hydrolysis:
Figure can't copy

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05:07

Problem 30

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
The following sequence illustrates how fatty acids are catabolized to acetyl coenzyme A, a process known as $\beta$-oxidation. Fill in the brackets.
Figure can't copy

Tom Rutherford
Tom Rutherford
Numerade Educator
04:26

Problem 31

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
Excessive accumulation of acetyl CoA can lead to metabolic ketosis by the following pathway:
Figure can't copy
$[\underline{\boldsymbol{A}}, \underline{\mathbf{B}}$, and $\underline{\boldsymbol{C}}$ (unfortunately!) are referred to as "ketone bodies;" accumulation of acids $\underline{\boldsymbol{A}}$ and $\underline{\boldsymbol{C}}$ lowers blood pH (acidosis).]

Lottie Adams
Lottie Adams
Numerade Educator

Problem 32

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate.
A cortisone story...

Cortisone is one of 43 steroids found in adrenal cortical glands. It was first isolated by Kendall (Mayo Clinic) in 1934 (extraction of $\sim 1,000 \mathrm{lbs}$ of beef adrenal glands yielded only $85-200 \mathrm{mg}$ of cortisone). One of the earliest total syntheses of cortisone was published by Sarett (Merck) in 1952. The following reactions illustrate his strategy.
a. The initial sequence of reactions formed the A-B-C rings. Draw the missing structures.
Figure can't copy
b. Construction of the D ring began as follows. Fill in the bracketed structure and outline the mechanism for step 3.
Figure can't copy
c. Subsequent selective reduction followed by tosylation produced the indicated structure, which was then treated with the sequence of reagents shown. Draw the product of step 2 and give the mechanism for step 3.
Figure can't copy
d. The above product was then subjected to the following steps. Draw structures for the critical intermediates in steps 2-4.
Figure can't copy
e. The final four steps yielded cortisone. Deduce the structure of cortisone acetate.
Figure can't copy

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Problem 33

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate
Figure can't copy $\xrightarrow[\text { 2. } \mathrm{H}_3 \mathrm{O}^{\oplus}, \Delta]{\text { 1. }{ }^{\ominus} \mathrm{OMe}, \mathrm{MeOH}}$

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Problem 34

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate
Figure can't copy

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Problem 35

Draw the structural formula of the major organic product(s). Show stereochemistry where appropriate
A step involving an intra-Michael reaction in Corey’s (Harvard) synthesis of longifolene, a component of Indian turpentine oil:
Figure can't copy

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