Concept explainers
(a)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with the lithium enolate of acetone followed by
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of acetone followed by
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of acetone followed by
Figure 1
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Lithium enolate of acetone attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of acetone followed by
(b)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with the lithium enolate of ethyl
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of ethyl
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of ethyl
Figure 2
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Lithium enolate of
The principal organic product obtained when isobutyraldehyde reacts with the lithium enolate of ethyl
(c)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with ethyl
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with ethyl
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with ethyl
Figure 3
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
The zinc metal converts the ethyl
The enolate ion generated attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
This reaction is a name reaction known as Reformatsky reaction.
The principal organic product obtained when isobutyraldehyde reacts with ethyl
(d)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with diethyl malonate and a secondary
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with diethyl malonate and a secondary amine
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with diethyl malonate and a secondary amine
Figure 4
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Malonic ester is converted into the enolate ion by the secondary amine taken as the catalyst. The secondary amine pyridine taken here is basic in nature and takes up the acidic proton of the malonic ester.
The enolate ion generated attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
This reaction is a name reaction known as Knoevenagal reaction.
The principal organic product obtained when isobutyraldehyde reacts with diethyl malonate and a secondary amine
(e)
Interpretation:
The principal organic product expected when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Concept introduction:
The nucleophilic addition reactions of carbonyl compounds are well known due to the polarity of the carbonyl group. The nucleophile attacks on the carbonyl and adds to the carbonyl carbon. The addition of enolate ion on the carbonyl compounds is known as aldol reaction.

Answer to Problem 22.57AP
The principal organic product obtained when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Explanation of Solution
The principal organic product obtained when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Figure 5
The enolate ions attack rapidly on the carbonyl group. The enolate ion attacks the carbonyl carbon from the carbon-side and undergoes addition on the carbonyl compound.
Ethyl acetoacetate is converted into the enolate ion by the secondary amine taken as the catalyst. The secondary amine pyridine taken here is basic in nature and takes up the acidic proton of the malonic ester.
The enolate ion generated attacks on the isobutyraldehyde from the carbon side and adds on the molecule. The acidic workup converts the oxide ion generated into alcohol group.
This reaction is a name reaction known as Knoevenagal reaction.
The principal organic product obtained when isobutyraldehyde reacts with ethyl acetoacetate and a secondary amine
Want to see more full solutions like this?
Chapter 22 Solutions
ORGANIC CHEMISTRY SAPLING ACCESS + ETEX
- What is the stepwise mechanism for this reaction?arrow_forward32. Consider a two-state system in which the low energy level is 300 J mol 1 and the higher energy level is 800 J mol 1, and the temperature is 300 K. Find the population of each level. Hint: Pay attention to your units. A. What is the partition function for this system? B. What are the populations of each level? Now instead, consider a system with energy levels of 0 J mol C. Now what is the partition function? D. And what are the populations of the two levels? E. Finally, repeat the second calculation at 500 K. and 500 J mol 1 at 300 K. F. What do you notice about the populations as you increase the temperature? At what temperature would you expect the states to have equal populations?arrow_forward30. We will derive the forms of the molecular partition functions for atoms and molecules shortly in class, but the partition function that describes the translational and rotational motion of a homonuclear diatomic molecule is given by Itrans (V,T) = = 2πmkBT h² V grot (T) 4π²IKBT h² Where h is Planck's constant and I is molecular moment of inertia. The overall partition function is qmolec Qtrans qrot. Find the energy, enthalpy, entropy, and Helmholtz free energy for the translational and rotational modes of 1 mole of oxygen molecules and 1 mole of iodine molecules at 50 K and at 300 K and with a volume of 1 m³. Here is some useful data: Moment of inertia: I2 I 7.46 x 10- 45 kg m² 2 O2 I 1.91 x 101 -46 kg m²arrow_forward
- K for each reaction step. Be sure to account for all bond-breaking and bond-making steps. HI HaC Drawing Arrows! H3C OCH3 H 4 59°F Mostly sunny H CH3 HO O CH3 'C' CH3 Select to Add Arrows CH3 1 L H&C. OCH3 H H H H Select to Add Arrows Q Search Problem 30 of 20 H. H3C + :0: H CH3 CH3 20 H2C Undo Reset Done DELLarrow_forwardDraw the principal organic product of the following reaction.arrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided structures, draw the curved arrows that epict the mechanistic steps for the proton transfer between a hydronium ion and a pi bond. Draw any missing organic structures in the empty boxes. Be sure to account for all lone-pairs and charges as well as bond-breaking and bond-making steps. 2 56°F Mostly cloudy F1 Drawing Arrows > Q Search F2 F3 F4 ▷11 H. H : CI: H + Undo Reset Done DELLarrow_forward
- Calculate the chemical shifts in 13C and 1H NMR for 4-chloropropiophenone ? Write structure and label hydrogens and carbons. Draw out the benzene ring structure when doing itarrow_forward1) Calculate the longest and shortest wavelengths in the Lyman and Paschen series. 2) Calculate the ionization energy of He* and L2+ ions in their ground states. 3) Calculate the kinetic energy of the electron emitted upon irradiation of a H-atom in ground state by a 50-nm radiation.arrow_forwardCalculate the ionization energy of He+ and Li²+ ions in their ground states. Thannnxxxxx sirrr Ahehehehehejh27278283-4;*; shebehebbw $+$;$-;$-28283773838 hahhehdvaarrow_forward
- Plleeaasseee solllveeee question 3 andd thankss sirr, don't solve it by AI plleeaasseee don't use AIarrow_forwardCalculate the chemical shifts in 13C and 1H NMR for 4-chloropropiophenone ? Write structure and label hydrogens and carbonsarrow_forwardPlease sirrr soollveee these parts pleaseeee and thank youuuuuarrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT


