ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Question
Chapter 26.5, Problem 18CC
Interpretation Introduction
Interpretation:
Octanol is more efficient than hexanol crossing cell membrane and entering a cell need to be explained.
Concept introduction:
A lipid bilayer is formed when phosphoglyceride self-assemble in water. The surface of the bilayer is polar and hence it is water soluble. The lipid bilayer is the main fabric of cell membrane. The lipid bilayer acts as a barrier which restrict the flow of water and ions through cell membranes. If the compound has a hydrophobic group means it can cross the non-polar environment and if a compound has hydrophilic group it cannot cross the non-polar environment.
To explain: why octanol is more efficient than hexanol at crossing cell membrane and entering a cell.
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Draw the corresponding structures in each of the boxes below:
Ester Name
Methyl butyrate
(Example)
Alcohol Structure
H3C-OH
Acid Structure
Ester Structure
Isoamyl acetate
Ethyl butyrate
Propyl acetate
Methyl salicylate
Octyl acetate
Isobutyl
propionate
Benzyl butyrate
Benzyl acetate
Ethyl acetate
H₂C
OH
HC
2) For each of the following reactions:
(i)
(ii)
Fill in the missing reactant, reagent, or product (s), indicating stereochemistry where
appropriate using dashed and wedged bonds.
If the reaction forms a racemic mixture, draw both structures in the box and write the
word "racemic".
(a)
(b)
1) R₂BH
2) H₂O2,
NaOH (aq)
HBr
Br
racemic
Br
+
Br Br
racemic
For each of the following reactions: Fill in the missing reactant, reagent, or product (s), indicating stereochemistry where appropriate using dashed and wedged bonds. If the reaction forms a racemic mixture, draw both structures in the box and write the word “racemic”.
Chapter 26 Solutions
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
Ch. 26.2 - Prob. 1CCCh. 26.2 - Prob. 2CCCh. 26.3 - Prob. 1LTSCh. 26.3 - Prob. 3PTSCh. 26.4 - Prob. 7CCCh. 26.4 - Prob. 8CCCh. 26.4 - Prob. 2LTSCh. 26.4 - Prob. 9PTSCh. 26.4 - Prob. 3LTSCh. 26.4 - Prob. 12PTS
Ch. 26.5 - Prob. 15CCCh. 26.5 - Prob. 16CCCh. 26.5 - Prob. 17CCCh. 26.5 - Prob. 18CCCh. 26.5 - Prob. 19CCCh. 26.6 - Prob. 20CCCh. 26.6 - Prob. 21CCCh. 26.6 - Prob. 22CCCh. 26.6 - Prob. 23CCCh. 26.7 - Prob. 24CCCh. 26.8 - Prob. 4LTSCh. 26.8 - Prob. 25PTSCh. 26.8 - Prob. 27CCCh. 26.8 - Prob. 28CCCh. 26 - Prob. 29PPCh. 26 - Prob. 30PPCh. 26 - Prob. 32PPCh. 26 - Prob. 33PPCh. 26 - Prob. 34PPCh. 26 - Prob. 35PPCh. 26 - Prob. 36PPCh. 26 - Prob. 37PPCh. 26 - Prob. 38PPCh. 26 - Prob. 39PPCh. 26 - Prob. 40PPCh. 26 - Prob. 41PPCh. 26 - Prob. 42PPCh. 26 - Prob. 43PPCh. 26 - Prob. 44PPCh. 26 - Prob. 45PPCh. 26 - Prob. 46PPCh. 26 - Prob. 47PPCh. 26 - Prob. 48PPCh. 26 - Prob. 49PPCh. 26 - Prob. 50PP
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