
(a)
Interpretation:
Mechanism for the conversion of compound (A) to compound (B) has to be given.
Concept Introduction:
Acid catalyzed reactions:
In an
(b)
Interpretation:
For the conversion of compound (B) to compound (C) reagents has to be proposed.
Concept Introduction:
Grignard addition:
It is an addition of organomagnesium halide to an
(c)
Interpretation:
Mechanism for the conversion of compound (C) to compound (D) has to be given.
Concept Introduction:
Acid catalyzed reactions:
In an organic synthesis reactions, most of the reactions are initiated by the abstraction of proton from acids by the reactant. Sulphuric acid is one of the reagent used for this purposes.
(d)
Interpretation:
For the conversion of compound (d) to amitriptyline reagents has to be proposed.
Concept Introduction:
SN2 reaction:
SN2 stands for bimolecular nucleophilic substitution reaction. In this type of reactions, simultaneous bond breaking and bond making steps are involved.
(e)
Interpretation:
The chirality of amitriptyline and the number of possible stereoisomers has to be checked.
Concept Introduction:
Stereoisomers and chiral:
Isomers differing only in their spatial arrangement of atoms are called as stereoisomers.
The geometric property of a molecule that cannot be superimposed on its mirror image is known as chirality. Chiral carbon is the one which is attached with four different groups or atoms.

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Chapter 22 Solutions
Student Study Guide and Solutions Manual for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- 34. Figure 3 shows Van Deemter plots for a solute molecule using different column inner diameters (i.d.). A) Predict whether decreasing the column inner diameters increase or decrease bandwidth. B) Predict which van Deemter equation coefficient (A, B, or C) has the greatest effect on increasing or decreasing bandwidth as a function of i.d. and justify your answer. Figure 3 Van Deemter plots for hydroquinone using different column inner diameters (i.d. in μm). The data was obtained from liquid chromatography experiments using fused-silica capillary columns packed with 1.0-μm particles. 35 20 H(um) 큰 20 15 90 0+ 1500 100 75 550 01 02 594 05 μ(cm/sec) 30 15 10arrow_forwardelow are experimentally determined van Deemter plots of column efficiency, H, vs. flow rate. H is a quantitative measurement of band broadening. The left plot is for a liquid chromatography application and the night is for gas chromatography. Compare and contrast these two plots in terms of the three band broadening mechanisms presented in this activity. How are they similar? How do they differ? Justify your answers.? 0.4 H (mm) 0.2 0.1- 0.3- 0 0.5 H (mm) 8.0 7.0 6.0 5.0 4.0- 3.0 T +++ 1.0 1.5 0 2.0 4.0 Flow Rate, u (cm/s) 6.0 8.0 Flow Rate, u (cm/s)arrow_forwardPredict the products of this organic reaction: + H ZH NaBH3CN H+ n. ? Click and drag to start drawing a structure. Xarrow_forward
- What is the missing reactant R in this organic reaction? + R H3O+ + • Draw the structure of R in the drawing area below. • Be sure to use wedge and dash bonds if it's necessary to draw one particular enantiomer. Click and drag to start drawing a structure.arrow_forwardWhat would be the best choices for the missing reagents 1 and 3 in this synthesis? 1 1. PPh3 2. n-BuLi 2 • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Click and drag to start drawing a structure.arrow_forwardThe product on the right-hand side of this reaction can be prepared from two organic reactants, under the conditions shown above and below the arrow. Draw 1 and 2 below, in any arrangement you like. 1+2 NaBH₂CN H+ N Click and drag to start drawing a structure. X $arrow_forward
- Explain what is the maximum absorbance of in which caffeine absorbs?arrow_forwardExplain reasons as to why the amount of caffeine extracted from both a singular extraction (5ml Mountain Dew) and a multiple extraction (2 x 5.0ml Mountain Dew) were severely high when compared to coca-cola?arrow_forwardProtecting Groups and Carbonyls 6) The synthesis generates allethrolone that exhibits high insect toxicity but low mammalian toxicity. They are used in pet shampoo, human lice shampoo, and industrial sprays for insects and mosquitos. Propose detailed mechanistic steps to generate the allethrolone label the different types of reagents (Grignard, acid/base protonation, acid/base deprotonation, reduction, oxidation, witting, aldol condensation, Robinson annulation, etc.) III + VI HS HS H+ CH,CH,Li III I II IV CI + P(Ph)3 V ༼ Hint: no strong base added VI S VII IX HO VIII -MgBr HgCl2,HgO HO. isomerization aqeuous solution H,SO, ༽༽༤༽༽ X MeOH Hint: enhances selectivity for reaction at the S X ☑arrow_forward
- Draw the complete mechanism for the acid-catalyzed hydration of this alkene. esc 田 Explanation Check 1 888 Q A slock Add/Remove step Q F4 F5 F6 A བྲA F7 $ % 5 @ 4 2 3 & 6 87 Click and drag to start drawing a structure. © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Ce W E R T Y U S D LL G H IK DD 요 F8 F9 F10 F1 * ( 8 9 0 O P J K L Z X C V B N M H He commandarrow_forwardExplanation Check F1 H₂O H₂ Pd 1) MCPBA 2) H3O+ 1) Hg(OAc)2, H₂O 2) NaBH4 OH CI OH OH OH hydration halohydrin formation addition halogenation hydrogenation inhalation hydrogenation hydration ☐ halohydrin formation addition halogenation formation chelation hydrogenation halohydrin formation substitution hydration halogenation addition Ohalohydrin formation subtraction halogenation addition hydrogenation hydration F2 80 F3 σ F4 F5 F6 1 ! 2 # 3 $ 4 % 05 Q W & Å © 2025 McGraw Hill LLC. All Rights Reserved. F7 F8 ( 6 7 8 9 LU E R T Y U A F9arrow_forwardShow the mechanism steps to obtain the lowerenergy intermediate: *see imagearrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic 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



