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(a)
Interpretation:
The structure of the cyclic anhydride formed by the given dicarboxylic acid when heated is to be drawn.
Concept introduction:
The term anhydride means “without water”. The anhydride can be formed of carboxylic acids either by using dehydrating agents or heating the
(b)
Interpretation:
The structure of the cyclic anhydride formed by the
Concept introduction:
The term anhydride means “without water”. The anhydride can be formed of carboxylic acids either by using dehydrating agents or heating the carboxylic acid. The formation of anhydrides of dicarboxylic acids resulting in the formation of five or six-membered ring structures is readily formed on heating.
(c)
Interpretation:
The structure of the cyclic anhydride formed by the given dicarboxylic acid when heated is to be drawn.
Concept introduction:
The term anhydride means “without water”. The anhydride can be formed of carboxylic acids either by using dehydrating agents or heating the carboxylic acid. The formation of anhydrides of dicarboxylic acids resulting in the formation of five or six-membered ring structures is readily formed on heating.
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Chapter 20 Solutions
EBK ORGANIC CHEMISTRY
- Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed tosynthesize the drug?arrow_forwardDraw the structure of the following: (a) p-chlorobenzoic anhydride (b) cis-3-Methylcyclohexanecarbonyl bromide (c) Ethyl 3-methylpentanoate (d) 3-chloro-N-ethyl-N-methylbenzamidearrow_forwardCholic acid, a major constituent of bile, has the structure shown.(a) Draw the structure of cholic acid, showing the rings in their chairconformations, and label each methyl group and hydroxy group asaxial or equatorial. (Making a model may be helpful.)(b) Cholic acid is secreted in bile as an amide linked to the aminogroup of glycine. This cholic acid–amino acid combination acts asan emulsifying agent to disperse lipids in the intestines for easierdigestion. Draw the structure of the cholic acid–glycine combination,and explain why it is a good emulsifying agent.arrow_forward
- Please draw the skeletal formula of the following compounds: (A) Isobutyraldehyde (B) α-Ethyl-γ-methoxycaproaldehyde (C) 6-Hydroxyhexanal (D) 2,4-Pentanedione (E)3-Cyano-7-oxoheptanoic acidarrow_forwardA key step in the synthesis of the narcotic analgesic meperidine (tradename Demerol) is the conversion of phenylacetonitrile to X. (a) What isthe structure of X? (b) What reactions convert X to meperidine ?arrow_forward9) a) Diagram the acid (H3O+) catalyzed enolizaton of acetaldehyde. . b) Diagram the base (OH-) catalyzed formation of cyclopentanone from its enol form.arrow_forward
- Draw the structures of the following carboxylic acids.(a) a@methylbutyric acid (b) 2-bromobutanoic acid(c) 4-aminopentanoic acid (d) cis-4-phenylbut-2-enoic acidarrow_forward(a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_forwardDraw line structures of the following compounds and the product you would obtain from the reduction of each.(a) Isopropyl methyl ketone (b) p-Hydroxybenzaldehyde(c) 2-Methylcyclopentanonearrow_forward
- Draw structures corresponding to the following names: (a) 3-hydroxyhexanoic acid (b) 2-iodo-2-methyloctanoic acid (c) 2-butynoic acid (d) 5-ethyl-6-oxoheptanoic acid (e) o-Hydroxybenzoic acid (f) cis-3-isopropylcyclohexanecarboxylic acidarrow_forward(a) Explain how NaBH4 in CH3OH can reduce hemiacetal A to butane-1,4-diol (HOCH2CH2CH2CH2OH). (b) What product is formed when A is treated with Ph3P = CHCH2CH(CH3)2? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects.arrow_forwardWhich is the stronger acid in each of the following pairs? Explain your reasoning. (a) Phenol or p-hydroxybenzaldehyde (b) m-Cyanophenol or p-cyanophenol (c) o-Fluorophenol or p-fluorophenolarrow_forward
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