
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Question
Chapter 21.6, Problem 22P
Interpretation Introduction
Interpretation:
Considering the partial retrosynthesis, the reaction mechanism for the synthesis of cyclopentyl methyl
Concept Introduction:
>A molecule that consists of a ketone group on the
Retrosynthesis is used to identify the reactants. It involves the breaking of the target molecule into starting materials.
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.. Give the major organic product(s) for each of the following reactions or sequences of reactions. Show
ll relevant stereochemistry [3 ONLY].
A
H Br 1. NaCN
2 NaOH, H₂O, heat
3. H3O+
B.
CH₂COOH
19000
1. LiAlH4 THF, heat
2 H₂O*
C.
CH Br
1. NaCN, acetone
2 H3O+, heat
D.
Br
1. Mg. ether 3. H₂O+
2 CO₂
E.
CN
1. (CH) CHMgBr, ether
2 H₂O+
Assign this COSY spectrum
Chapter 21 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 21.1 - Prob. 1PCh. 21.1 - Prob. 2PCh. 21.1 - Prob. 3PCh. 21.1 - Prob. 4PCh. 21.1 - Prob. 5PCh. 21.2 - Prob. 6PCh. 21.2 - Prob. 7PCh. 21.2 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.3 - Prob. 10P
Ch. 21.3 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - Problem 21.15 Write the structure of the Dieckmann...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.6 - Prob. 18PCh. 21.6 - Prob. 19PCh. 21.6 - Prob. 20PCh. 21.6 - Prob. 21PCh. 21.6 - Prob. 22PCh. 21.7 - Prob. 23PCh. 21.8 - Problem 21.24 Mesityl oxide is an industrial...Ch. 21.8 - Prob. 25PCh. 21.8 - Prob. 26PCh. 21.8 - Prob. 27PCh. 21.8 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Terreic acid, a naturally occurring antibiotic...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Give the structure of the expected organic product...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Give the structure of the principal organic...Ch. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - Prob. 45PCh. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - The use of epoxides as alkylating agents for...Ch. 21 - Prob. 49PCh. 21 - Show how you could prepare each of the following...Ch. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - The - methylene ketone sarkomycin has an...Ch. 21 - - Lactone can be prepared in good yield from...Ch. 21 - Prob. 57PCh. 21 - Prob. 58DSPCh. 21 - The Enolate Chemistry of Dianionss The synthetic...Ch. 21 - Prob. 60DSPCh. 21 - Prob. 61DSPCh. 21 - Prob. 62DSPCh. 21 - Prob. 63DSP
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- Can I please get help with this?arrow_forward1. Draw structures corresponding to each of the following names [3 ONLY]: A. 2,2,2-trichloroethanal (chloral). B. trans-3-isopropylcyclohexanecarbaldehyde C. What is the correct structure for 2-hydroxyacetophenone? Circle the letter of your response. a C 0 OH OH OH HO b. H3C CH 0 H d OH D. Provide IUPAC names for each structure below. 0 H C-H 0 0 CH3 H NO₂ E. The substance formed on addition of water to an aldehyde or ketone is called a hydrate or a/an: a. vicinal diol b. geminal diol C. acetal d. ketalarrow_forwardAssign this spectrumarrow_forward
- Redraw the tripeptide with or without its acidic hydrogensto demonstrate where the total charge of -2 comes from: *see imagearrow_forward2. 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 + H₂Oarrow_forwardAssign all integrated peaksarrow_forward
- - 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
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