Fill in the empty blanks and spaces in the table. The structure of d-galactose is in the next picture for reference. STRUCTURE OF SUGARDERIVATIVE PRODUCEDNAME OF SUGARDERIVATIVEPRODUCEDTYPE OF SUGARREACTANTSDERIVATIVED-galactoseBenedict'sCHOн-с-онD-galactoseно-с-н+HO-C-Hн-с-онCOOHD-galactosegalactitol C-HCH2OHH =C-OHOHHO-C-Hонно-с нH-C-OHa-D-galactopyranoseCH2OHD-galactose

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Answered: STRUCTURE OF SUGAR DERIVATIVE PRODUCED…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter25: Biomolecules: Carbohydrates

Section25.6: Reactions Of Monosaccharides

Problem 17P

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5. Which two D-pentose sugars give optically active alditols when reduced with NABH4 CHO н— он CH2OH D-glyceraldehyde. Сно CHO H HOH H HOH CH2OH „D-erythrose HO H H HOH ČH2OH D-threose CHO CHO CHO CHO -OH HO-H H OH Но -O- H +OH но -H но- H- HFOH CH2OH H- -OH H +OH H FOH CH2OH CH2OH ČH2OH D-ribose D-arabinose D-хylose D-lyхose CHO CHO CHO CHO Сно CHO CHO CHO HO-H HO-H HO-H H HOH но—н но—н H FOH H HOH H +OH HO-H H FOH H- -O- HO-H но- H OH H- -O- но но—н H FOH HO-H H +OH CH2OH H HOH H -OH H HOH H FOH но FH HHOH ČH2OH HHOH ČH2OH H- -OH H -OH H- -OH -OH ČH2OH ČH2OH CH2OH CH2OH ČH2OH D-allose D-altose D-glucose D-mannose D-gulose D-idose D-galactose D-talose
The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed. сно сно сно CH2OH C=0 H- OH H- -OH но- H- но H- "OH но H- Но H- но H- H- -H- H20 H- HO- O- H- -O- H- -OH -O- OH ČHOH CH,OH ČH2OH ČH2OH (recovered starting material) D-glucose
CHO -Н НО- HO-H H-OH Н -ОН CH₂OH What is the relationship between these two sugars? НО CHO -Н H-OH HO-H но- -Н CH₂OH A) identical structures B) enantiomers C) diastereomers D) constitutional isomers E) non-isomeric
5) Draw the following sugars in BOTH the alpha and beta pyranose form: C-H Но H- Но C-H HO H- НО H- ОН H- ОН А. CH2OH H- ОН H- ОН CH2OH CH2OH C=0 НО H- H- ОН H Но- CH2OH 'CH,OH c=0 НО- H. H- ОН H- OH CH2OH
Which of the following is a keto-pentose ? * Н CH₂OH Н 0 НО c=0 НО- HO НО 3 O Р « 00 D H HO ОН Н CH₂OH (A) н- НО C -ОН -Н CH OH (В) C - Н Н O. 1 5 HHH Н -H CH₂OH (c) Н 0 с HO-H HO H H OH Н ОН CH₂OH (D)
Two sugars differing in configuration at a single asymmetric carbon atom are known as epimers. D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of glucose. Structure Il and IIl are H- -OH но- -H H OH HO H но- H HO H H -OH H- -OH HO OH H -OH H- -OH H OH HO. HO, OH II II Which of the following represents an aldopentose? OH H O HO O HO H но н HO H но- HO H HO H HO- H OH H OH H OH H OH OH HO Он of но" HO O OH он III IV These are chemical messengers that are secreted by endocrine glands and carried through the bloodstream to target tissues. prostaglandin deoxysugar glycoside hormones Which of the following is NOT correctly paired? cellulose: beta-1,4-glycosidic linkage amylose: alpha-1,4-glycosidic linkage chitosan: alpha-1,4-glycosidic linkage cellubiose: beta-1,4-glycosidic linkage
a) Which of the following monosaccharides will react with Tollens' reagent? Circle all that аpply. СООН CH2OH CH2OH OCH3 но- H- ОН HO FH OH CH2OH CH2OH OH II III IV V b) Decide whether the disaccharide shown below is a reducing or non-reducing sugar CH2OH но Но- ОН CH2 но Но OH OH 우 오
1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.
Draw the product formed when pentanal (CH3CH2CH2CH2CHO) is treatedwith following reagent. With some reagents, no reaction occurs. [1] HC≡CNa; [2] H2O
Determine whether each structure is an enantiomer or a diastereomer of D-xylose. Н НО Н CHO -ОН -Н -ОН CH₂OH D-Xylose НО H Н CHO -Н -OH -ОН CH₂OH Н- НО НО CHO -ОН H -H CH2OH HO H НО CHO -Н -ОН -Н CH2OH
Draw α-l-tagatopyranose :
Predict the products obtained when d-galactose reacts with each reagent. (h) NaBH4(i) Br2, H2O, then H2O2 and Fe2(SO4)3

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