Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 25.10, Problem 27P
Interpretation Introduction
Interpretation:
In cholesterol
Concept introduction:
Cholesterol is a steroid abundant in animals. It is an important component in cell membrane. The ring structure is rigid. Cholesterol has eight asymmetric centers, 256 stereoisomers are possible, but only one exist in nature.
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The following is the structure of salicin, a bitter-tasting compound found in the bark of willow trees: The aromatic ring portion of this structure is quite insoluble in water. How would forming a glycosidic bond between the aromatic ring and β - D -glucose alter the solubility?
Which of the following is D-glucose?
HO-C-H
H-C-OH
H-C-OH
HO-C-H
H-C-OH
HO-C-H
H-C-OH
H-C-OH
H-C-OH
H-C-OH
H-C-OH
H-C-OH
H-C-OH
H-C-OH
I
CH2OH
CH2OH
CH2OH
CH₂OH
A
B
C
D
OA
OB
O C
OD
Provide the IUPAC name for the following tetrasaccharide.
но-
HO
но
но-
но-
но,
но-
HO
но
но.
OH
Chapter 25 Solutions
Organic Chemistry, Books a la Carte Edition (8th Edition)
Ch. 25.1 - Prob. 1PCh. 25.3 - Which has a higher melting point, glyceryl...Ch. 25.3 - Draw the structure of an optically inactive fat...Ch. 25.3 - Draw the structure of an optically active fat...Ch. 25.5 - Do the identities of R1 and R2 in phosphatidic...Ch. 25.5 - Membranes contain proteins, Integral membrane...Ch. 25.5 - Prob. 8PCh. 25.5 - The membrane phospholipids in deer have a higher...Ch. 25.6 - Treating PGC2 with a strong base such as sodium...Ch. 25.7 - Mark off the isoprene units in menthol, -selinene,...
Ch. 25.7 - Prob. 13PCh. 25.7 - Prob. 14PCh. 25.8 - Propose mechanisms for the Claisen condensation...Ch. 25.8 - Prob. 16PCh. 25.8 - Propose a mechanism for the conversion of...Ch. 25.8 - Propose a mechanism for the biosynthesis of...Ch. 25.8 - Propose a mechanism for the conversion of the E...Ch. 25.8 - The fluoro-substitued geranyl pyrophosphate shown...Ch. 25.8 - Prob. 22PCh. 25.8 - Prob. 23PCh. 25.9 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 25.10 - Prob. 26PCh. 25.10 - Prob. 27PCh. 25.10 - The acid component of a cholesterol ester is a...Ch. 25.10 - Prob. 29PCh. 25.10 - Prob. 30PCh. 25 - Prob. 31PCh. 25 - An optically active fat, when completely...Ch. 25 - Prob. 33PCh. 25 - a. How many different triacylglycerols are there...Ch. 25 - Cardiolipins are found in heart muscles. Draw the...Ch. 25 - Nutmeg contains a simple, fully saturated...Ch. 25 - Draw the product that is obtained from the...Ch. 25 - Prob. 39PCh. 25 - Prob. 40PCh. 25 - Propose a mechanism for the biosynthesis of...Ch. 25 - 5-Androstene-3.17-dione is isomerized to...Ch. 25 - Prob. 44PCh. 25 - Eudesmol is a sesquiterpene found in eucalyptus....Ch. 25 - Prob. 46PCh. 25 - Prob. 47PCh. 25 - Diethylstilbestrol (DES) was given to pregnant...
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- Describe the glycosidic bonds in dermatan sulfatearrow_forwardWhich compounds are d-monosaccharides? Which are l-monosaccharides?arrow_forwardIdentify the type of glycosidic bond in the following disaccharide. CH,OH H H ОН Н CH2 H H H ОН Н HO ОН H. ОН HO H H OH O B-1,4-glycosidic bond O a-1,4-glycosidic bond O B-1,6-glycosidic bond O a-1,6-glycosidic bondarrow_forward
- in the following molecule the glycosidic bond is circled. CH2OH CH2OH H CH2OH OH HO H H НО H. ОН ÓH True Falsearrow_forwardDescribe each glycosidic bond in this trisaccharide.arrow_forwardDraw the structure of the expected product when monosaccharide A undergomutarotation upon dissolving in water in the presence of Tollens reagent (AgNO3,NH4OH).arrow_forward
- Classify each monosaccharide according to the position of the carbonyl group and the number of carbon atoms in the molecule. CHO CH₂OH OH H -OH CH,OH aldotriose aldotetrose aldopentose ketotetrose ketotriose ketopentose galactose ketopentose aldotetrose ketotetrose ketohexose aldohexose aldopentose OH OH aldotetrose aldopentose ketohexose aldohexose ketopentose ketotetrosearrow_forwardConsider two disaccharides OH CH₂OH OH maltose OH CH OH OH - OH OH OH CH₂OH OH fructose OH OH CH OH Which of the two disaccharides contains a hemiacetal? Which of the two disaccharides contains the acetal? CHLOH OHarrow_forwardD The following disaccharide contains a(n) (blank]-glycosidic linkage. HO CH₂OH ОН Oa-1,4 OB-1,4 a-1,6 O B-1,6 0 OH Question 6 double bond ssignments/syllabus ester bond ether bond amide bond HO A glycosidic bond between two monosaccharides can also be classified as a(n) [blank). OH OH Melebi OH MacBook Proarrow_forward
- Following is the Haworth structure of a disaccharide. Identify the type of glycosidic bond in this disaccharide. CH₂OH H HO H OH H H OH H H a-1,6-glycosidic bond O a,B-1,2-glycosidic bond O B-1,4-glycosidic bond O a-1,4-glycosidic bond CH₂OH H OH H H OH H OH B a hparrow_forwardN-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Nearrow_forwardIdentify the type(s) of glycosidic bonds in digitoxin / digoxin.arrow_forward
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