Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 43P
Interpretation Introduction
Interpretation:
The explanation for physical property (here, boiling point) of a compound based on its structural formula is to suggested.
Concept introduction:
The
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b) Disaccharide E is a reducing sugar. It is hydrolyzed by an α-glycosidase enzyme, which means it contains an α-
glycoside link. Treatment of E with Ag2O and excess Mel gives an octamethyl derivative F. Hydrolysis of F in
dilute aqueous acid gives the pair of molecules shown below. Write the structures of E and F. (If the
stereochemistry at a particular carbon is not determined by the above data, indicate this with a wavy line as
shown below.)
HO OMe
OMe
Is is
MeO
MeO
MOH
OMe
mOH
OMe
OMe
b) Compounds A and B have the following properties:
Compound A (C5H1005) is an optically active D-pentose that exists exclusively as an acyclic molecule. (Hint:
that sentence alone completely determines the structure of A! But we generously give you more information.)
• Compound A does not react with Br₂/H₂O.
• Reduction of A with NaBH4 gives only one product, B (C5H12O5), which is optically active.
Write acyclic Fischer projection structures of A and B.
What is the product (from the image below) of the starting material D-glyceraldehyde which will
(1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3
(2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3
Chapter 22 Solutions
Organic Chemistry, 12e Study Guide/Student Solutions Manual
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...
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- Some of the most important organic compounds in biochemistry are the α-amino acids, represented by the general formula shown.Write structural formulas for the following α-amino acids.(a) Alanine (R = methyl)(b) Valine (R = isopropyl)(c) Leucine (R = isobutyl)(d) Isoleucine (R = sec-butyl)(e) Serine (R = XCH2, where X is the functional group that characterizes alcohols)(f) Cysteine (R = XCH2, where X is the functional group that characterizes thiols)(g) Aspartic acid (R = XCH2, where X is the functional group that characterizes carboxylic acids)arrow_forward(a) A certain lipid has the structure shown below (R1 and R2 are fatty acyl chains). Could a sample of these molecules form a bilayer? Why or why not? (b) Would phospholipase A1 be able to use this molecule as a substrate? Why or why not?arrow_forward(a) Is the compound CH3CH≡CH2 saturated or unsaturated?Explain. (b) What is wrong with the formulaCH3CH2CH≡CH3?arrow_forward
- Draw the structure of leu-enkephalin, a pentapeptide that acts as an analgesic and opiate, and has the following sequence: Tyr–Gly–Gly–Phe–Leu. (The structure of a related peptide, met-enkephalin, appeared in Section 22.6B.)arrow_forwardThis unit is N-acetylneuraminic acid, the most abundant member of a family of amino sugars containing nine or more carbons and distributed widely throughout the animal kingdom. Draw the open-chain form of this amino sugar. Do not be concerned with the configuration of the five chiral centers in the open-chain form.arrow_forwardHexadecyltrimethylammonium chloride, CH3(CH2)15N(CH3)+3 Cl-, is one of a class of cationic detergents, commonly used inshampoos and as “clothes rinses.”(a) Identify the hydrophilic head group and the hydrophobic tail.(b) Draw a depiction of a micelle that would form if this compound were dissolved in water.(c) What are the intermolecular forces that are primarily responsible for the micelle’s solubility in water?arrow_forward
- The tea leaves that contain the caffeine to be isolated are predominantly composed of cellulose, a natural and extremely abundant polymer of glucose. Look up the chair structure of B-D-glucose (B-D-glucopyranose, the monomer from which the cellulose polymer is composed). Draw this structure, draw the flipped chair, and indicate which conformer you think is more stable, if either. BRIEFLY explain your choice.arrow_forward1.When 2-heptyne was treated with H2SO4(aqueous) containing mercuric sulphate, two products, each having molecular formula C7H14O, were obtained in approximately equal amounts. (a) What are these two products and write down their structures (b) Write a complete reaction equation.arrow_forwardCystine is an amino acid formed from the oxidation of twocysteine molecules to form a disulfide bond. The molecular formula of cystine is C6H12O4N2S2. Draw the structural formula of cystine. (arrow_forward
- DRAW THE CHEMICAL STRUCTURE OF THE FOLLOWING:1) Methyl 5-methyl-6-oxohexanoate2) 5-Amino-3-methylpentan-2-ol3) Isopropyl 3-hydroxypropanoate4) 3-Oxocyclohexanecarbaldehyde5) 5-Methyl-6-oxohexanamide6) p-Chloromethylbenzene7) 2,5,5-Trimethyl-4-oxohept-2-enoic acidarrow_forwardHERE IS THE DESCRIPTION: Start with the condensed structural formula CH3-C(CH3)=CH-C(CH3)2-CH(CH3)2 and react it first with H₂O in the presence of H₂SO4 (as the catalyst), to produce a major substrate product. Then, take that major substrate product, and use it as the substrate of the next reaction, by reacting it with K₂Cr2O7 and H₂SO4, to produce the FINAL MAJOR substrate product. The complete correct condensed structural formula for the major substrate product (after reaction step 1) is (CH3)2CHOHCH2C (If no new product is formed in this step, type "no reaction.") The complete correct condensed structural formula for the final major substrate product (after reaction step 2) is C9H1801 (If no new product is formed in this step, type "no reaction.")arrow_forward(a) What is the difference between the hormones progesterone and testosterone? (b) Draw the structure of a a steroid nucleus. (c) Give the products obtained from complete base hydrolysis in the following reaction: O || CH,−O−C−(CH2)14–CH3 O CH–0–C−(CH2)14—CH3 + 3 NaOH O CH,−0–C−(CH2)14–CH3arrow_forward
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