EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 9781260475685
Author: SMITH
Publisher: MCGRAW-HILL HIGHER EDUCATION
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Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see image
2. Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of α-hydroxycarboxylic acids from ketones and
aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid.
Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin
is treated with aqueous base the original carbonyl compound is isolated.
OH
CH-COOH
0
HO CN
C
H30*
C.
H
H
HC N
NaOH
H₂O
C=O
0
cyanohydrin
H
+ NaCN + H₂O
Assign all integrated peaks
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- - Consider the data in the Table below to answer the following questions: Acidities of Substituted Benzoic and Acetic Acids pk,s at 25C Y-CH COOH Y Y - CH₂COOH meta para H 4.75 4.19 4.19 2.47 3.64 3.55 3.57 4.09 4.46 CN OCH 3 A. Draw the structure of the strongest acid in the table above. B. Explain why cyanoacetic acid and methoxyacetic acid are more acidic than their correspondingly substituted benzoic acid counterparts.arrow_forwardDraw the curved arrow mechanism for this reaction starting with 2-propanol in sulfuric acid. Show all nonzero formal charges and all nonbonded electrons in each step. Species not involved in a particular step do not need to be included in that step, and resonance forms do not need to be shown. Note that the alcohol is in much higher concentration than H₂O in this reaction. Harrow_forwardProvide reactions showing the following conversions: * see imagearrow_forward
- . Draw structures corresponding to each of the following names or Provide IUPAC names for each of the ollowing structures [for 4 ONLY]. A. 2-propylpentanoic acid. B. m-chlorobenzoic acid. D. C. O O HOC(CH2)3COH glutaricadd OH OH H3C CH3 C=C H COOH salicylicadd tiglicadd CH₂C=N Joe Marrow_forward. Provide structure(s) for the starting material(s), reagent(s) or the major organic product(s) of each of the ollowing reactions or sequences of reactions. Show all relevant stereochemistry [five only] A. O B. OET CH3 1. LIAIH, ether 2 H₂O O (CH3)2CH-C-CI + 0 0 ether (CH3)2CH-C-O-C-CH3 CH3 C. 0 OH HO CH3 ° Clarrow_forwardHow would you prepare each of the following compounds using either an acetoacetic ester synthesis or a alonic ester synthesis? Show all intermediate structures and all reagents.[Three only] A. B. COOH OH C. D. 0 H2C CHCH2CH2CCH3arrow_forward
- Fats and greases have mostly aliphatic regions which are hydrophobic. Provide a schematic of howsoaps/detergents remove fats and grease from the soiled material. * see imagearrow_forwardWhat chemical has the common name "lye"? Pick one of the 3 esters and show the hydrolysis mechanism to make a carboxylic acid. The organic “R” should be used to limit the redrawing time of the entire molecule. * see imagearrow_forwardProvide the products for each reaction. There are two and they are not related. *see imagearrow_forward
- d. a phenylal Give the major organic product(s) of each of the following reactions or sequences of reactions. Show all levant stereochemistry. [three only] 0 A. B. CH3 Bra CH3COOH OH 1. Br₂, PBrz 2 H₂O 12arrow_forward2arrow_forwardShow how the following conversions might be accomplished. Show all reagents and all intermediate ructures. More than one step may be required [2 ONLY]: A. B. ° C. OH 0 OH 0arrow_forward
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