Amines are nitrogen-containing organic molecules derived from ammonia (NH3). Which compound is more soluble in water—CH3CONHCH3 or 2-methylbutane [CH3CH(CH3)CH2CH3)]? Explain. The -ic ending of the common name or the -oic ending of the International Union of Pure and Applied Chemistry (IUPAC) name of the carboxylic acid is replaced with the suffix -amide. Explain. Write the condensed structural formulas and names of the two compounds from which CH3CH2CH2CH2CH2CONHCH2CH2CH3 is formed. 5. With the exception of formamide (HCONH2), which is a liquid, all simple amides are solids (Table 5.2 "Physical Constants of Some Unsubstituted Amides"). Write the equation for the hydrolysis of each compound. Which compound is more soluble in water—benzoic acid or sodium benzoate? (For more about peptide linkages, see Chapter 8 "Amino Acids", Section 8.3 "Peptides".). Identify the general structure for an amine. Crack cocaine is more volatile than cocaine hydrochloride. Draw the structures for the five isomeric amines that have the molecular formula C7H9N and contain a benzene ring. For example, compare the boiling point of methylamine (CH3NH2; −6°C) with those of ethane (CH3CH3; −89°C) and methanol (CH3OH; 65°C). The location of substituents along the carbon chain is indicated by a Greek letter (for common names) or a number (for names from the International Union of Pure and Applied Chemistry). This leaves the user in a pleasureless state and (often) craving more cocaine. Many heterocyclic compounds are important in medicine and biochemistry. (For more information about proteins, see Chapter 9 "Proteins and Enzymes", Section 9.1 "Proteins".). 2. CH3CH2CH2CH2COOH (pentanoic acid) and NH3 (ammonia). Figure 5.1 The Structure of Amines Compared to Water, an Alcohol, and an Ether. Many drugs that are amines are converted to hydrochloride salts to increase their solubility in aqueous solution. (The third bond on the nitrogen atom goes to a hydrogen atom.). There are many heterocyclic amines, including many physiologically important ones. The benzene ring with an amino (NH2) group is aniline. You can & download or print using the browser document reader options. 1. Amide molecules can engage in hydrogen bonding with water molecules (a). Nearly all amines, including those that are not very soluble in water, will react with strong acids to form salts soluble in water. This website works best with modern browsers such as the latest versions of Chrome, Firefox, Safari, and Edge. Classify each compound as primary, secondary, or tertiary. 9. Its mechanism of action is not well understood, but it is thought to block the activity of adenosine, a heterocyclic base that acts as a neurotransmitter, a substance that carries messages across a tiny gap (synapse) from one nerve cell (neuron) to another cell. Draw the structure for 2-amino-3-methylpentane. Dicarboxylic acids have two carboxyl groups and are named with the ending -dioic acid. Identify the functional group for amines. Butyramide thus yields butyric acid and ammonia. Give the equation for the reaction of 1,5-pentanedioic acid (HOOCCH2CH2CH2COOH; common name, glutaric acid) with each of the following: 7. The compound is named as a derivative of aniline: 3-bromoaniline or m-bromoaniline. Amines of low molar mass are quite soluble in water; the borderline of solubility in water is at five or six carbon atoms. Write the condensed structural formulas and give names of the two compounds from which butanamide (CH3CH2CH2CONH2) is formed. Write the condensed structural formulas and names of the two compounds from which pentanamide (CH3CH2CH2CH2CONH2) is formed. Draw the structure for p-isopropylaniline and classify. Some prefer to ingest their cocaine by smoking it (mixed with tobacco, for example). The name indicates that there are an isopropyl group (in red) and two methyl groups (in green) attached to the nitrogen atom; the amine is tertiary. 4. How many milliliters of a 0.100 M barium hydroxide solution are required to neutralize 0.500 g of dichloroacetic acid? What products are obtained when CH3CH2CH2CH2CONH2 is hydrolyzed in an hydrochloric acid solution? Because aldehydes are formed from primary alcohols, these alcohols are also a starting material for carboxylic acids. b. α-methylbutyramide (2-methylbutanamide), Chapter 1 - Organic Chemistry Review / Hydrocarbons, Chapter 2 - Alcohols, Phenols, Thiols, Ethers, Chapter 10 - Nucleic Acids and Protein Synthesis, Chapter 11 - Metabolic Pathways and Energy Production, CHE 120 - Introduction to Organic Chemistry - Textbook, 5.7 Chemical Properties of Amides: Hydrolysis, Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License. Found worksheet you are looking for? See Chapter 10 "Nucleic Acids and Protein Synthesis".). Thus, although isopropylamine looks similar to isopropyl alcohol, the former is a primary amine, while the latter is a secondary alcohol. Click here to view some great books which can aid your learning . 2. The amine functional group is as follows: 1. For example, CH3NH3+ is the methylammonium ion. 1. People ingest this drug by smoking or chewing tobacco. Caffeine is a stimulant found in coffee, tea, and some soft drinks. Explain. There are two methyl groups and one ethyl group on the nitrogen atom. In this lipids, amines, and amides worksheet, students answer nine questions about formulas and structures of these molecules. They also complete chemical equations giving the products of the reactions. Name the typical reactions that take place with amines. These studies provide the necessary background for more applied courses, such as anatomy and physiology, exercise physiology, kinesiology, and nutrition. Make sure that your printout includes all content from the page. Amides of five or fewer carbon atoms are soluble in water?. Generally, amides resist hydrolysis in plain water, even after prolonged heating. If 3.00 g of acetic acid reacts with excess methanol, how many grams of methyl acetate are formed? These characteristics and their solubility in water result from the polar nature of the amide group and hydrogen bonding (Figure 5.3 "Hydrogen Bonding in Amides"). pentanamide because the nitrogen-to-hydrogen (N–H) and the carbon-to-oxygen double (C=O) bonds can engage in hydrogen bonding; propyl acetate cannot engage in hydrogen bonding, propanamide because the N–H and C=O bonds can engage in hydrogen bonding with water; 1-pentene cannot engage in hydrogen bonding with water. 10. You can & download or print using the browser document reader options. 2. Their names are as follows: To what inorganic compound are the amines related? If one or both of the two remaining bonds on the atom are attached to alkyl or aryl groups, the compound is a substituted amide. Showing top 8 worksheets in the category - Naming Amides And Amines. It comes from acetic acid (CH3COOH). Like other amines, these compounds are basic. CH3CH2CH2COOH (butanoic acid) and NH3 (ammonia), CH3CH2CH2CH2CH2COOH (hexanoic acid) and CH3CH2CH2NH2 (propylamine). Carboxylic acids have strong, often disagreeable, odors. The amine functional group is as follows: Amines are named by naming the alkyl groups attached to the nitrogen atom, followed by the suffix -amine. Showing top 8 worksheets in the category - Nomenclature Amines. Name amides according to the IUPAC system. Explain. An ester with the molecular formula C6H12O2 was hydrolyzed in aqueous acid to yield an acid Y and an alcohol Z. Oxidation of the alcohol with potassium dichromate (K2Cr2O7) gave the identical acid Y. Those amides with a hydrogen atom on the nitrogen atom can also engage in hydrogen bonding (b). Unless otherwise noted, this work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License. The OH of acetic acid is replaced by an NH, This amide is derived from benzoic acid. There are many familiar carboxylic acids. Compare the boiling points of amides with alcohols of similar molar mass. Worksheet will open in a new window. 2. The monomers condense by splitting out water to form a new product, which is still difunctional and thus can react further to yield a polyamide polymer. They are readily absorbed through the skin, and workers must exercise caution when handling these compounds. All three classes of amines can engage in hydrogen bonding with water (part (b) of Figure 5.2 "Hydrogen Bonding"). Identify the functional group for an amide. Explain why the boiling points of primary and secondary amines are higher than those of alkanes or ethers of similar molar mass but are lower than those of alcohols. Heterocyclic amines are cyclic compounds with one or more nitrogen atoms in the ring. Describe the preparation procedure for amides. The neutralization of 125 mL of a 0.400 M NaOH solution requires 5.10 g of a monocarboxylic acid. The amino group (NH2) is named as a substituent in more complicated amines, such as those that incorporate other functional groups or in which the alkyl groups cannot be simply named. Always start with the parent compound: draw the pentane chain.
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