DOCSLIB.ORG

United States Patent Office Patented July 2, 1957 1

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
United States Patent Office Patented July 2, 1957 1 2,798,090 United States Patent Office Patented July 2, 1957 1. 2. A particular feature of our invention is that nitro ; benzene can be sulfonated to meta-nitrobenzene sulfonic 2,798,090 acid and the meta-nitrobenzene sulfonic acid thus formed PROCESS FOR PRE PARNG BENZALANILENE-3- is used without isolation from its reaction mixture in the SULEONCACED COMP8UNDS preparation of the benzalaniline-3-sulfonic acid com Max W. Krell and Flaven E. Johnson, Kingsport, Texin, pounds. This is a big improvement over the hydrochloric assignors to Eastman Kodak CoEspany, Rochester, acid process wherein meta-nitrobenzene, sulfonic acid is N.Y., a corporation of New Jersey formed by sulfonating nitrobenzene with sulfuric acid, isolated from its reaction mixture, and then reacted with No Drawing. Application March 2, 1953, O formaldehyde and an aniline compound in the presence Serial No. 339,923 of hydrochloric acid in that the meta-nitrobenzene sui fonic acid does not have to be separately recovered and 12 Claims. (C. 260-509) the sulfuric acid present in the sulfonation operation supplies the sulfuric acid used in the reaction between This invention relates to an improved process for pre 15 the aniline compound, formaldehyde and meta-nitro paring benzalaniline-3-sulfonic acid compounds which in benzene sulfonic acid. Additionally, the advantages their free acid form have the formula: above enumerated with respect to better yields, lower (I) R costs and reduced corrosion are also obtained. The reaction between the aniline compound, formalde / 20 hyde and meta-nitrobenzene Sulfonic acid in the presence R of sulfuric acid and iron is preferably carried out at a SOs temperature of from 5 C. to 35° C. A temperature of wherein X stands for a monocyclic aryl nucleus of the from about 16° C. to about 20° C. appears to be espe benzene series and R and R1 each represents an alkyl cially advantageous. Similarly, the iron is preferably group, a hydroxyalkyl group or an alkoxyalkyl group and 25 added as fast as foaming and temperature control will wherein the group permit and preferably should not take over 3 hours. R Following the conditions just set forth, product yields of Y 80% or more are normally obtained. The reaction has been carried out at temperatures as low as 0° C. and as 30 high as 50 C. with the addition of iron taking up to 8 stands in para position to the hours but conditions falling outside the preferred range B ordinarily give much inferior results to those obtained -C=N grouping - when the prefered conditions are employed. grouping. The aryl nucleus X may be substituted by substituents It is an object of this invention to provide an improved 35 such as, for example, the methyl group, the ethyl group, process for preparing benzalaniline-3-sulfonic acid.com a methoxy group, an ethoxy group, a chlorine atom or a pounds having the formula above given, whereby these bromine atom. Illustrative of the alkyl groups repre compounds are efficiently and economically prepared in sented by R and R1 are the methyl, the ethyl, the n-propyi, good yield. A particular object is to provide a new and the isopropyl and the n-butyl groups. Illustrative of the improved process for preparing said benzalaniline-3- 40 hydroxyalkyl groups represented by R and R1 are the sulfonic acid compounds using nitrobenzene as a starting (3-hydroxyethyl group, the 6-hydroxypropyl group, the compound. y-hydroxypropyl group, the 6, y-dihydroxypropyl group 4'-(ethylg-hydroxyethyl)aminobenzalaniline-3-sulfonic and the 8-hydroxybutyl group. Similarly, the 3-methoxy acid, 4'-(butyl, 6-hydroxyethyl)aminobenzalaniline-3- ethyl and the 3-ethoxyethyl groups are illustrative of the sulfonic acid and 4'-(butyl, p-hydroxyethyl)amino-2'- 45 alkoxyalkyl groups R and R1 represent. methylbenzalaniline-3-sulfonic acid have been prepared Illustrative of the aniline compounds having the by reacting N-ethyl-N-3-hydroxyethylaniline, N-butyl-N- formula numbered II are N,N-di-3-hydroxyethylaniline, B-hydroxyethylaniline and N-butyl-N-(3-hydroxyethyl-m- N,N-di-3-hydroxyethyl-m-toluidine, N,N-di- (3-hydroxy toluidine, respectively, with formaldehyde and sodium ethyl- m - ethylaniline, N-ethyl-N-3-hydroxyethylaniline, meta-nitrobenzene, sulfonate in the presence of hydro N,N-dimethylaniline, N,N-diethylaniline, N,N-di-n- chloric acid and iron. Dippy, Hogarth, Watson and propylaniline, N,N-di-n-butylaniline, N,N-di-6-methoxy Williams, J.Soc. Chem. Ind., vol. 56, pages. 346T-348T ethylaniline, N,N-di-g-ethoxyethylaniline, N,N-di-3-hy (1937). ... droxyethyl-m-chloroaniline, N,N-di- (3-hydroxyethyl-m- We have discovered that the benzalaniline-3-sulfonic methoxyaniline, N-ethyl-N-3-hydroxyethyl-m-toluidine, acid compounds having the formula numbered. I can be 55 N-6-hydroxyethyl-N-(3-ethoxyethylaniline, N-n-butyl-N-6- prepared by reacting aniline compounds having the -hydroxyethylaniline, N-ethyl-N-y-hydroxypropylaniline, formula: N-ethyl-N-8-hydroxybutylaniline, N-ethyl- N - 6,y-dihy droxypropylaniline, N-n-propyl-N-6, y-dihydroxypropyl (II) R m-toluidine, N,N-di-3, y-dihydroxypropyl-m-toluidine, N 60 methyl-N-6-hydroxyethyl-m-toluidine, N,N-di-6-hydroxy ethyl-m-bromoaniline, N,N-di-y-hydroxypropyl-m-bromo wherein X, R and R1 have the meaning previously as aniline and N,N-di-3-hydroxybutyl-m-chloroaniline. signed to them with formaldehyde and meta-nitrobenzene "The following examples, in which parts are expressed sulfonic acid in the presence of sulfuric acid. and iron. 65 as parts by weight, illustrate the process of our invention. The aniline compound is not substituted in the para position to the amino group. The use of Sulfuric acid Example 1 in place of hydrochloric acid gives. much better yields 123 parts of nitrobenzene, were slowly, added, with and results in much lower costs for producing these good agitation to. 460 parts of 20% oleum at 50° C. By products. Additionally, the use of sulfuric acid rather 70 the time addition of the nitrobenzene was complete the than hydrochloric acid considerably reduces the problem temperature of the reaction mixture had risen to 75, C.- of corrosion. 80° C. Following the addition of the nitrobenzene the 2,798,090 3 4 reaction mixture was heated very slowly to 95 C. and reaction mixture was stirred for four hours at 16 C-20 maintained at 95 C. for two hours after which it was C. and then filtered after decanting the reaction mixture allowed to cool to room temperature. from any unreacted iron. The product, 4'-(di-6-hydroxy 214 parts of the meta-nitrobenzene sulfonic acid re ethylamino)-2'-chlorobenzalaniline-3-sulfonic acid was re action mixture prepared as described above were added covered on the filter as an orange solid. It was washed to 545 parts of water and then 49 parts of N,N-di-6- well with water and dried. 77 parts (80% yield) of hydroxyethyl-m-toluidine were dissolved in the resulting dried product were obtained. mixture. The reaction mixture thus obtained was cooled The benzalaniline-3-sulfonic acid compounds set forth to 20 C. and 27 parts of 36% aqueous formaldehyde in the tabulation given hereinafter are likewise readily were added thereto. 56 parts of iron filings were then O prepared in accordance with the process of our invention added to the reaction mixture during approximately two using the procedure described hereinbefore. In each case hours while maintaining the temperature between 16° C. the benzalaniline-3-sulfonic acid compound and the ani and 20 C. After the iron addition was complete, the line compound from which it is prepared is given. reaction mixture was stirred for four hours at 16° C.- 20 C. and then filtered after decanting the reaction mix 15 Benzalaniline-3-Sulfonic Acid Compound Aniline Compound ture from any unreacted iron. 4'-(di-3-hydroxyethyl amino)-2'-methylbenzalaniline-3-sulfonic acid having the 6. 4 - (di- 6 - hydroxyethylamino)-2'- N,N- d - 3 - hydroxyethyl methoxybenzalaniline-3-sulfonic acid. n-methoxyaniline. formula: 7. 4 - (di-g-hydroxyethylamino)-2'- N,N-di- 3-hydroxyethyl ethoxybenzaaniline-3-sulfonic acid. m-ethoxyaniline. HOCH, CH, 8. 4- (di- 3-hydroxyethylamino)-2'- N,N-di- 6 - hydroxyethyl 20 ethylbenzalaniline-3-sulfonic acid. methylaniline. 9. 4 - (dinnethylamino) benzalaailine-3- N,N-dimethylaniline. - / sulfonic acid. - HOCC 10. 4.- (dimethylamino)-2-methylben N,N-dimethylamino - m - CE SOE zal-aniline-3-sulfonic acid. toluidine. 1. 4 - (diethylamino)-2-methylben - N,N - diethylamino - m was recovered as an orange solid, washed well with water za-aniline-3-sulfonic acid. toluidine. and dried. 85.5 parts (90% yield) of dried product were 25 12. 4 - (di-n - propylamino) benzalani N,N-di-n-propylaniline. line-3-sulfonic acid. obtained, 13. 4- (di-n - butylamino) benzalani N,N-di-n-butylaniline. Example 2 line-3-sulfonic acid. 4. 4- (di- 3-methoxyethylamino)-2'- N,N-di- B - methoxyethyl By use of 45 parts of N,N-di-3-hydroxyethylaniline in methylbenzalaniline-3-sulfonic acid. m-toluidine, 15. 4.- (di-6- ethoxyethylamino) benzal N,N- di - 6 - ethoxyethyl place of N,N-di-6-hydroxyethyl-m-toluidine in Example aniline-3-sulfonic acid, aniline. 1, 81 parts (89% yield) of 4'-(dig-hydroxyethylamino)- 30 16. 4 - (ethyl, S - hydroxyethyl) annino N - ethyl - N - 3 - hydroxy benzalanine-3-sulfonic acid, ethylaniline. benzalaniline-3-sulfonic acid were obtained. 17. 4.- (n-propyl, 3-hydroxyethyl)am N-n-propyl-N-5-hydroxy inobenzalaniline-3-sulfonic acid. ethylamiline. Example 3 18. 4- (n-butyl, 3-hydroxyethyl) an N-n-butyl-N-B-hydroxy ethylaniline. Example 1 was repeated using 41 parts of N-ethyl-N- 19.ind-benzalaniline-3-sulfonic 4- (ethyl, y -hydroxypropyl)amino acid.
Load more

Recommended publications
  • Common Names for Selected Aromatic Groups
    More Nomenclature: Common Names for Selected Aromatic Groups Phenyl group = or Ph = C6H5 = Aryl = Ar = aromatic group. It is a broad term, and includes any aromatic rings. Benzyl = Bn = It has a -CH2- (methylene) group attached to the benzene ring. This group can be used to name particular compounds, such as the one shown below. This compound has chlorine attached to a benzyl group, therefore it is called benzyl chloride. Benzoyl = Bz = . This is different from benzyl group (there is an extra “o” in the name). It has a carbonyl attached to the benzene ring instead of a methylene group. For example, is named benzoyl chloride. Therefore, it is sometimes helpful to recognize a common structure in order to name a compound. Example: Nomenclature: 3-phenylpentane Example: This is Amaize. It is used to enhance the yield of corn production. The systematic name for this compound is 2,4-dinitro-6-(1-methylpropyl)phenol. Polynuclear Aromatic Compounds Aromatic rings can fuse together to form polynuclear aromatic compounds. Example: It is two benzene rings fused together, and it is aromatic. The electrons are delocalized in both rings (think about all of its resonance form). Example: This compound is also aromatic, including the ring in the middle. All carbons are sp2 hybridized and the electron density is shared across all 5 rings. Example: DDT is an insecticide and helped to wipe out malaria in many parts of the world. Consequently, the person who discovered it (Muller) won the Nobel Prize in 1942. The systematic name for this compound is 1,1,1-trichloro-2,2-bis-(4-chlorophenyl)ethane.
    [Show full text]
  • P-Chloro-O-Toluidine and Its Hydrochloride Al
    Report on Carcinogens, Fourteenth Edition For Table of Contents, see home page: http://ntp.niehs.nih.gov/go/roc p-Chloro-o-toluidine and Its Hydrochloride al. 1979, Bentley et al. 1986, IARC 2000). In organs from animals ex- posed to p-chloro-o-toluidine, DNA breakage was detected by single- CAS Nos. 95-69-2 and 3165-93-3 cell gel electrophoresis (comet assay) in mouse liver, urinary bladder, lung, and brain and in rat liver and kidney (Sekihashi et al. 2002). Reasonably anticipated to be human carcinogens First listed in the Eighth Report on Carcinogens (1998) Properties Also known as 4-chloro-o-toluidine or 4-chloro-2-methylaniline p-Chloro-o-toluidine is a chlorinated aromatic amine that exists as a grayish-white crystalline solid or leaflet, andp -chloro-o-toluidine hy- CH3 drochloride is a buff-colored or light-pink powder at room tempera- ture. The base compound is practically insoluble in water or carbon NH2 tetrachloride but is soluble in ethanol or dilute acid solutions. It is stable under normal temperatures and pressures (Akron 2009). Phys- Cl ical and chemical properties of p-chloro-o-toluidine are listed in the following table. No physical and chemical properties for the hydro- Carcinogenicity chloride were found except its molecular weight of 178.1 and melt- p-Chloro-o-toluidine and its hydrochloride salt are reasonably antic‑ ing range of 265°C to 270°C (IARC 2000, Weisburger 1978). ipated to be human carcinogens based on limited evidence of carci- Property Information nogenicity from studies in humans and evidence of carcinogenicity Molecular weight 141.6a from studies in experimental animals.
    [Show full text]
  • PDMS-Based Antimicrobial Surfaces for Healthcare Applications
    PDMS-based Antimicrobial Surfaces for Healthcare Applications This thesis is presented to UCL in partial fulfilment of the requirements for the Degree of Doctor of Philosophy Ekrem Ozkan Supervised by Professor Ivan P. Parkin Materials Chemistry Research Centre Dr Elaine Allan Division of Microbial Diseases 2017 1 DECLARATION I, Ekrem Ozkan confirm that the work presented in this thesis is my own. Where information has been derived from other sources, I confirm that this has been indicated in the thesis. 2 ABSTRACT This thesis describes two types of approaches for reducing the incidence of hospital- acquired infections (HAIs), which are chemical approaches that inactivate bacteria that adhere to the surface i.e. bactericidal activity and physical approaches that inhibit initial bacterial attachment to the surface i.e. anti-biofouling activity. Specifically, the antimicrobial polydimethylsiloxane (PDMS)-based systems detailed in this thesis are: (i) photosensitizer, crystal violet (CV),-coated PDMS for both medical device and hospital touch surface applications, (ii) crystal violet-coated, zinc oxide nanoparticle-encapsulated PDMS for hospital touch surface applications, (iii) superhydrophobic antibacterial copper coated PDMS films via aerosol assisted chemical vapour deposition (AACVD) for hospital touch surface applications and (iv) slippery copper-coated PDMS films to prevent biofilm formation on medical devices. The materials were characterized using techniques including: X-ray diffraction (XRD), scanning electron microscopy (SEM), UV-vis absorbance spectroscopy, water-contact angle measurement and microbiology tests. Functional testing indicated that CV-coated samples were suitable for targeted applications and showed potent light-activated antimicrobial activity when tested against model Gram-positive bacteria, Staphylococcus aureus, and Gram-negative bacteria, Escherichia coli, associated with hospital-acquired infections, with > 4 log reduction in viable bacterial numbers observed.
    [Show full text]
  • Ortho-TOLUIDINE
    ortho-TOLUIDINE 1. Exposure Data 1.1 Chemical and physical data 1.1.1 Nomenclature Chem. Abstr. Serv. Reg. No.: 95–53–4 CAS Name: 2-Methylbenzenamine Synonyms: 1-Amino-2-methylbenzene; 2-amino-1-methylbenzene; 2-aminotoluene; ortho-aminotoluene; 2-methyl-1-aminobenzene; 2-methylaniline; ortho-methylaniline; ortho-methylbenzenamine; 2-methylphenylamine; 2- tolylamine; ortho-tolylamine 1.1.2 Structural formula, molecular formula, and relative molecular mass NH2 CH3 C7H9N Rel. mol. mass: 107.15 1.1.3 Chemical and physical properties of the pure substance Description: Light yellow liquid becoming reddish brown on exposure to air and light (O’Neil, 2006) Boiling-point: 200–201 °C (O’Neil, 2006) Melting-point: −14.41 °C (Lide, 2008) Solubility: Slightly soluble in water; soluble in diethyl ether, ethanol and dilute acids (O’Neil, 2006) Octanol/water partition coefficient: log P, 1.29–1.32 (Verschueren, 2001) –407– 408 IARC MONOGRAPHS VOLUME 99 1.1.4 Technical products and impurities No information was available to the Working Group. 1.1.5 Analysis ortho-Toluidine is the most widely studied of the aromatic amines reviewed in this Volume. Waste-water, air and urine samples have been analysed. The use of LC/MS and LC with electrochemical detection provides detection limits down to the nanomol level. ortho-Toluidine is one of the amines detected as a reduction product of azo dyes used as toy colourants. Table 1.1 presents selected methods of detection and quantification of ortho-toluidine in various matrices. Table 1.1. Selected methods of analysis of ortho-toluidine in various matrices Sample Sample preparation Assay method Detection limit Reference matrix Toys Sodium dithionite HPLC/UV 0.2 μg/g Garrigós et al.
    [Show full text]
  • EXPERIMENT 2 SEPARATION of a MIXTURE of P-TOLUIDINE AND
    EXPERIMENT 2 1:: SEPARATION OF A MIXTURE OF p-TOLUIDINE AND NAPHTHALENE BY SOLVENT EXTRACTION AND IDENTI- FICATION OF THEIR FUNCTIONAL GROUPS 4: 2.1 Introduction Objectives - 2.2 Principle 2.3 Requirements Identification of functional.groups 2.5 Result 2.1 INTROD-UCTION In the previous experiment you have separated a mixture containing two acidic and one neutral compound. The extracting solutions were aqueous bases. In this experiment you will be seperating a mixture of a basic and a neutral compound. As you will recall from sec. 1.2 of experiment 1 that this will require an aqueous'acidic solution. The basic compound after separation is recovered by re extraction. Objeetives After srudying and performing this experiment you should be able to : . separate a mixture of a neutral and a basic organic compound by solvent extraction technique, identify the functional group of the separated compounds, and describe the theory behind the above. 2.2 PRINCIPLE This mixture contains a basic compound, p-toluidine, and a neutral compound viz., naphthalene. Their separation is quite straight forward. You will recall from above that a basic compound can be extracted by an aqueous solution of an acid. As this mixture contains only one basic compound (as against two acidic compounds in the previous experiment), you don't need to bother about which acid to use for extraction. A strong acid like HCI is definitely a good choice and will afford an effective separation. The hydrochloric acid will convertp-toluidine into its hydrochloride salt which on extraction will moFVeinto aqueous layer. Separation of a Mixture of p-Toluidine and Naphthakne by Solvent Extraction and IdenH- Ucatkm dthelr FuaEtiooal C~P Q NII: HCI NI I,C'I- - + NH2 @-toluidine) @-tohidine hydrochldride) p-Toluidine Freep-toluidine can be recovered by hydrolping this salt with an aqueous base.
    [Show full text]
  • Organic Chemistry Nomenclature Guide
    Chemistry 222 Organic Chemistry Nomenclature Guide Many molecules in organic chemistry can be named using alkyl groups. MEMORIZE THEM! Common Alkyl (R) Groups Number of Carbons Formula Name 1 -CH3 methyl 2 -CH2CH3 ethyl 3 -CH2CH2CH3 propyl 4 -CH2CH2CH2CH3 butyl 5 -CH2CH2CH2CH2CH3 pentyl 6 -CH2(CH2)4CH3 hexyl 7 -CH2(CH2)5CH3 heptyl 8 -CH2(CH2)6CH3 octyl 9 -CH2(CH2)7CH3 nonyl Alkyl groups are generically referred to as R-groups, where R could be a methyl group, ethyl group, octyl group, etc. Organic compounds are often lumped into families or classes of compounds. The classes we will study this term include the following: R H R O H R O R R X Alcohols Ethers Alkanes Cycloalkanes Alkyl Halides or haloalkanes O O C C C C R C R C R H Ketones Aldehydes Alkynes Alkenes Aromatics H O O O All of these families are detailed in the R N R C R C R C pages that follow. H O H O R NH2 Amides Amines Carboxylic Acids Esters Page IV-20-1 / Organic Chemistry Nomenclature Guide Alkanes Elemental Formula: CnH2n+2 H Nomenclature Guidelines: -yl on alkyl group, +ane to ending Notes: An alkane is an alkyl group plus a hydrogen, often referenced as R-H. H C H Alkanes contain only carbon and hydrogen atoms in long chains with no rings. Each 3 H carbon atom is sp hybridized. Alkanes make great fuels but are generally unreactive. methane, CH4 Example: CH4 - methane - is a methyl group plus a hydrogen (CH3-H) Example: C2H6 - ethane - is a ethyl group plus a hydrogen (CH3CH2-H) Cycloalkanes H Elemental Formula: CnH2n H Nomenclature Guidelines: cyclo+ -yl on alkyl group, +ane to ending C H Notes: Cycloalkanes are alkanes which form an internal ring within the H C C molecule.
    [Show full text]
  • Perkin's Mauve: the History of the Chemistry
    REFLECTIONS Perkin’s Mauve: The History of the Chemistry Andrew Filarowski Those of us who owe our living in part to the global dyestuff and chemical industry should pause today and remember the beginnings of this giant industry which started 150 years ago today with William Perkins’ discovery of mauveine whilst working in his home laboratory during the Easter holiday on April 28, 1856. Prior to this discovery, all textiles were dyed with natural dyestuffs and pigments. What did Perkin’s Reaction Entail? William Henry Perkin carried out his experiments at his home laboratory in the Easter break of 1856. He was trying to produce quinine (C20H24N2O2). This formula was known but not the structural formula. Because chemistry was in such an early stage of development Perkin thought that by simply balancing the masses (simple additive and subtractive chemistry) in an equation he would obtain the required compound. He therefore believed that if he took two allyltoluidine molecules, C10H13N, and oxidised them with three oxygen atoms (using potassium dichromate) he would get quinine (C20H24N2O2) and water. 2 (C10H13N) + 3O C20H24N2O2 + H2O It is unsurprising to us now but Perkin reported “that no quinine was formed, but only a dirty reddish brown precipitate.” However, he continued in his trials and decided to use aniline (C6H5NH2) and its sulphate, and to oxidise them using potassium dichromate. This produced a black precipitate that Perkin at first took to be a failed experiment, but he noticed on cleaning his equipment with alcohol that a coloured solution was obtained. Perkin’s Patent W H Perkin filed his patent on the 26th August 1856 for “Producing a new colouring matter for the dyeing with a lilac or purple color stuffs of silk, cotton, wool, or other materials.” (sic) Patent No.
    [Show full text]
  • Ester Synthesis Lab (Student Handout)
    Name: ________________________ Lab Partner: ____________________ Date: __________________________ Class Period: ____________________ Ester Synthesis Lab (Student Handout) Lab Report Components: The following must be included in your lab book in order to receive full credit. 1. Purpose 2. Hypothesis 3. Procedure 4. Observation/Data Table 5. Results 6. Mechanism (In class) 7. Conclusion Introduction The compounds you will be making are also naturally occurring compounds; the chemical structure of these compounds is already known from other investigations. Esters are organic molecules of the general form: where R1 and R2 are any carbon chain. Esters are unique in that they often have strong, pleasant odors. As such, they are often used in fragrances, and many artificial flavorings are in fact esters. Esters are produced by the reaction between alcohols and carboxylic acids. For example, reacting ethanol with acetic acid to give ethyl acetate is shown below. + → + In the case of ethyl acetate, R1 is a CH3 group and R2 is a CH3CH2 group. Naming esters systematically requires naming the functional groups on both sides of the bridging oxygen. In the example above, the right side of the ester as shown is a CH3CH2 1 group, or ethyl group. The left side is CH3C=O, or acetate. The name of the ester is therefore ethyl acetate. Deriving the names of the side from the carboxylic acid merely requires replacing the suffix –ic with –ate. Materials • Alcohol • Carboxylic Acid o 1 o A o 2 o B o 3 o C o 4 Observation Parameters: • Record the combination of carboxylic acid and alcohol • Observe each reactant • Observe each product Procedure 1.
    [Show full text]
  • NOMENCLATURE of ORGANIC COMPOUNDS ©2010, 2003, 1980, by David A
    NOMENCLATURE OF ORGANIC COMPOUNDS ©2010, 2003, 1980, by David A. Katz. All rights reserved. Organic chemistry is the chemistry of carbon compounds. Carbon has the ability to bond with itself to form long chains and, as a result, millions of compounds from simple hydrocarbons to large biomolecules such as proteins, lipids, carbohydrates, and nucleic acids. Originally it was believed that these compounds had to come from a living organism, now they are synthesized in the laboratory. The simplest organic compounds are composed of carbon and hydrogen and are known as hydrocarbons. There are four types, or classes, of hydrocarbons: Alkanes: contain all C-C single bonds. These are known as saturated hydrocarbons. Alkenes: contain at least one C=C double bond. Alkynes: contain at least one C≡C triple bond. Both alkenes and alkynes are known as unsaturated hydrocarbons Aromatic hydrocarbons: contain a benzene structure Lewis structures of alkanes look like this: These are also called structural formulas. Since these take up a lot of space, condensed structural formulas are used. Even simpler than condensed structures are skeletal or line structures: There are a range of structures used to represent organic compounds: Before we start naming organic compounds, it is important to understand how carbon atoms are bonded. Every carbon atom will try to form 4 bonds. A carbon atom on the end of a chain of single bonded carbon atoms will be bonded to H one carbon atom and three hydrogen atoms: C C H H 1 H A carbon atom in the middle of a chain of single bonded carbon atoms will be H bonded to two carbon atoms and two hydrogen atoms.
    [Show full text]
  • Chapter 16 the Chemistry of Benzene and Its Derivatives
    Instructor Supplemental Solutions to Problems © 2010 Roberts and Company Publishers Chapter 16 The Chemistry of Benzene and Its Derivatives Solutions to In-Text Problems 16.1 (b) o-Diethylbenzene or 1,2-diethylbenzene (d) 2,4-Dichlorophenol (f) Benzylbenzene or (phenylmethyl)benzene (also commonly called diphenylmethane) 16.2 (b) (d) (f) (h) 16.3 Add about 25 °C per carbon relative to toluene (110.6 C; see text p. 743): (b) propylbenzene: 161 °C (actual: 159 °C) 16.4 The aromatic compound has NMR absorptions with greater chemical shift in each case because of the ring current (Fig. 16.2, text p. 745). (b) The chemical shift of the benzene protons is at considerably greater chemical shift because benzene is aromatic and 1,4-cyclohexadiene is not. 16.6 (b) Among other features, the NMR spectrum of 1-bromo-4-ethylbenzene has a typical ethyl quartet and a typical para-substitution pattern for the ring protons, as shown in Fig. 16.3, text p. 747, whereas the spectrum of (2- bromoethyl)benzene should show a pair of triplets for the methylene protons and a complex pattern for the ring protons. If this isn’t enough to distinguish the two compounds, the integral of the ring protons relative to the integral of the remaining protons is different in the two compounds. 16.7 (b) The IR spectrum indicates the presence of an OH group, and the chemical shift of the broad NMR resonance (d 6.0) suggests that this could be a phenol. The splitting patterns of the d 1.17 and d 2.58 resonances show that the compound also contains an ethyl group, and the splitting pattern of the ring protons shows that the compound is a para-disubstituted benzene derivative.
    [Show full text]
  • Organic and Biological Chemistry
    CHAPTER 23 Organic and Biological Chemistry CONTENTS HO H 23.1 ▶ Organic Molecules and Their C Structures: Alkanes H H C 23.2 ▶ Families of Organic Compounds: HO O O C C Functional Groups 23.3 ▶ Naming Organic Compounds H CC 23.4 ▶ Carbohydrates:HO A Biological Example HO OH of Isomers H 23.5 ▶ Valence Bond TCheory and Orbital OverlapH Pictures H C 23.6 ▶ Lipids:HO A Biological EOxample ofO Cis–Trans IsomerismC C 23.7 ▶ Formal Charge and Resonance in Organic CompoundsH CC 23.8 ▶ Conjugated SystemsHO OH 23.9 ▶ Proteins: A Biological Example of Conjugation 23.10 ▶ Aromatic Compounds and Molecular Ascorbic acid, also known as vitamin C, is an essential nutrient in the human diet Orbital Theory because it is not synthesized in our body. We can eat citrus fruits or take pills that contain vitamin C to maintain health. 23.11 ▶ Nucleic Acids: A Biological Example of Aromaticity ? Which Is Better, Natural or Synthetic? The answer to this question can be found in the INQUIRY ▶▶▶ on page 1021. STUDY GUIDE M23_MCMU3170_07_SE_C23.indd 978 27/11/14 2:11 AM f the ultimate goal of chemistry is to understand the world around us on a molecular level, then a knowledge of biochemistry—the chemistry of living organisms—is a central part Iof that goal. Biochemistry, in turn, is a branch of organic chemistry, a term originally used to mean the study of compounds from living organisms while inorganic chemistry was used for the study of compounds from nonliving sources. Today, however, we know that there are no fundamental differences between organic and inorganic compounds; the same principles apply to both.
    [Show full text]
  • Biosynthesis of Quinine and Related Alkaloids EDM-ARI)LEETE
    February 1060 I~IOSYNTHESISOF QUINIXE AND l1ELATE:L) XLKALO1I)S 50 Biosynthesis of Quinine and Related Alkaloids EDM-ARI)LEETE Department oj Chenaisli.y, Ilniversitij of Minnesota, ilfinneapoIis, I1mnesotu 6,i/+ R~eizpdSeptendw ,I, 1968 The antimalarial drug quinine (1) has had a fascinat- years old at the timc of hwvestirig for quinirie extr:ic- ing history.’ In 1820 it was isolated in a crystalline tion. state from the bark of a Cinchona tree by l’elletier T’ortunately from our point of view, cjuiniiic mid and Caventou.2 In 1856 I’erltin, having little infor- other alkaloids are biosynthe*ized in young seedlings. mation on the alkaloid except its molecular formula, This was evident from the work of de Jloerloo~,~ attempted to obtain it by oxidizing allyltoluidine with who cultivated l-year-old Czr~chomsuccii-ubi~ p1:Lrit.: potassium dichromate according to in a11 atmosphere containing radioactive carbon dioxide and obtained radioactive quinine from the p1:mts. 2CioHiBN + 30 + C+NzO, + HzO allyltolkiidiiie yiiinine The biogenetic relationship of the indole illkdoids cin- Seedless to say, this attempt was unsuccessful and choriamine and quiriamine was suggested by Chuttirel, yielded a dirty reddish brown precipitate. However, et UZ.,~ and a plausible biogenetic scheme based on this the results of this experiment led Perkin to investigate view, upon Turner and Wood\vitrd’sg ideaq, arid oil the oxidation of simpler amines, and from the oxidation tracer work to be described is illustrated in Scheme I. of crude aniline (which contained some toluidine) he It is suggested that tryptophan (or possibly trypt- obtained the first synthetic dye, mauve (2),which was amine’O) condenses with the nine-carbon triuldehyde used for dyeing silk and coloring postage stamps in the 3 (the origin of this unit will be discussed later) to 186O’~.~ afford the tetrahydro-@-carbolinederivative 4.
    [Show full text]