Concept explainers
(a)
Interpretation:
The product formed by the reaction of D-galactose with
Concept Introduction:
The reaction of
(a)
Explanation of Solution
The D-galactose is an aldohexose molecule. The carbonyl group present in D-galactose is
The formed alditol is optically inactive as it is a meso compound and shows plane of symmetry.
(b)
Interpretation:
The product formed by the reaction of D-galactose with
Concept Introduction:
The reagent
(b)
Explanation of Solution
When the D-galactose molecule is made to react with
The formed alditol is optically inactive as it is a meso compound and it shows plane of symmetry.
(c)
Interpretation:
The product formed by the reaction of D-galactose with warm
Concept Introduction:
The reaction of warm
(c)
Explanation of Solution
The nitric acid (
The product formed is a meso compound and shows plane of symmetry. So, it is optically inactive.
(d)
Interpretation:
The product formed by the reaction of D-galactose with
Concept Introduction:
The reaction of
(d)
Explanation of Solution
When the D-galactose reacts with
The formed product is optically active.
(e)
Interpretation:
The product formed by the reaction of D-galactose with
Concept Introduction:
The reaction of
(e)
Explanation of Solution
The D-galactose molecule consumes
The products formed are achiral and are optically inactive.
(f)
Interpretation:
The product formed by the reaction of D-galactose with aniline (
(f)
Explanation of Solution
The D-galactose molecule reacts with aniline molecule and the aldehyde group of carbohydrate is reacted with the
The formed product is a chiral compound and optically active.
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Chapter 25 Solutions
Organic Chemistry
- Predict the products obtained when d-galactose reacts with each reagent. (c) CH3OH, H + (d) Ag(NH3) 2+ -OH(e) H2, Niarrow_forwardThe following observations are obtained after a D-hexose was made to react with several reagents: (1) The reactions of a D-hexose with (a) to (d) below yields an aldaric acid (a) NH₂OH, (b) (CH3CO)₂O, NaOCOCH 3, and, (c) NaOCH3, and then, (d) HNO3, H₂O (2) HNO3 oxidation of the same D-hexose gives an aldaric acid. Predict the structures of the three (3) possible hexoses that can undergo the above reactions?arrow_forwardWhich D-aldopentoses are reduced to optically inactive alditols using NaBH,, CH;OH?arrow_forward
- Draw Fischer projections for the product(s) formed by reaction of d-galactose with the following. In addition, state whether each product is optically active or inactive. Q.) HNO3, warmarrow_forward1. 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.arrow_forwardConsider the structure of raffinose, a trisaccharide found in sugar beets and a number of higher plants. HO CH,OH Но- OH OCH, Но Но OH НОСН Но CH,OH ÓH raffinose (a) Classify raffinose as a reducing or nonreducing sugar, and tell how you know. (b) Identify the glycoside linkages in raffinose, and clas- sify each as either a or B. (c) Name the monosaccharides formed when raffinose is hydrolyzed in aqueous acid. (d) What products are formed when raffinose is treated with dimethyl sulfate in NaOH, and then with aqueous acid and heat?arrow_forward
- Draw Fischer projections for the product(s) formed by reaction of d-galactose with the following. In addition, state whether each product is optically active or inactive. Q.) H2/Ptarrow_forwardDraw Fischer projections for the product(s) formed by reaction of d-ribose with the following. In addition, state whether each product is optically active or inactive Q. HNO3, warmarrow_forwardA. Classify each of the following monosaccharides as aldose or ketose. (a) H. (b) CH2OH (c) CH2OH (d) H. C=0 C=0 HO-C-H H-C-H H-C-OH HO-C-H H-C-OH H-C-OH H-C-OH HO-C-H CH2OH H-C-OH CH2OH H-C-OH | CH2OH CH2OH Threose Ribulose Tagatose 2-Deoxyribosearrow_forward
- Lactose is a disaccharide in which a glycosidic linkage connects the monosaccharides galactose and glucose. OH НО OH (a) Identify the glycosidic linkage and the acetal carbon in lactose. (b) What type of glycosidic linkage does lactose have (i.e., is it 1,1'-, 1,2'-, etc., and is it a or B)? (c) People who are lactose intolerant are deficient in the enzyme lactase, and therefore cannot efficiently break down the disaccharide into its monosaccharides. When lactose is treated with aqueous acid, however, this hydrolysis can take place, though relatively slowly. Draw the complete, detailed mechanism and the products of the acid-catalyzed hydrolysis of lactose. Но ОН НО ОН ОН Lactosearrow_forwardPredict the products obtained when d-galactose reacts with each reagent. (d) Ag(NH3) 2+ -OH(e) H2, Ni (f) excess Ac2O and pyridinearrow_forward5. Provide suitable responses for questions (a) – (). 6 CH2OH 4 OH OH 3 OH (a) What is the relative configuration of the above monosaccharide? (b) Which labeled carbon is the anomeric carbon? (c) Trace and identify the acetal in the above monosaccharide. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H. OH O. OH CH,OH OH OHarrow_forward