There are two dicarboxylic acids with the general formula
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- Rank the following substances in order of increasing acidity: (a) (CH3)2CHOH, HC≡CH, (CF3)2CHOH, CH3OH (b) Phenol, p-methylphenol, p-[trifluoromethyl) phenol (c) Benzyl alcohol, phenol, p-hydroxybenzonic acidarrow_forwardIndicate the products A and B that are obtained in the following reactions: OH CH3 + HOCH2-CH₂OH + TSOH → A 1° NaH/THF A + →> B 2º C6H5-CH2Cl Briefly comment on each reaction.arrow_forward1 2 3 4 Draw The Structures? Z-Butenedioic acid (maleic acid) 2,5-Dimethylbenzoic acid Z-2-Chloro-3-phenyl-2- propenoic acid (cis-B- chloroallocinnamic acid) Decanedioic acid (sebacic acid) E-3-Phenyl-2-propenoic acid (trans-cinnamic acid)arrow_forward
- Two methods convert an alkyl halide into a carboxylic acid having one more carbon atom. (1] R-X + "CN R-CN R,COOH COOH (Section 22.18) + X- new C-C bond [1] CO2 RCOOH (Section 20.14) [2] H3O [2] R-X + Mg R-MgX Depending on the structure of the alkyl halide, one or both of these methods may be employed. For each alkyl halide, write out a stepwise sequence that converts it to a carboxylic acid with one more carbon atom. If both methods work, draw both routes. If one method cannot be used, state why it can't. Br a. CH,CI b. c. (CH3)3CCI d. HOCH,CH,CH,CH,Brarrow_forwardKetones and aldehydes react with sodium acetylide (the sodium salt of acetylene) to give alcohols, as shown in the following example: R, OH 1. HC=C: Na* 2. Hзо C. R2 R2 HC Draw the structure of the major reaction product when the following compound reacts with sodium acetylide, assuming that the reaction takes preferentially from the Re face of the carbonyl group. Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it.arrow_forwardExplain why phenol (C6H50H) is substantially more acidic than methanol (CH3OH), but benzoic acid (C6H5CO2H) is not much more acidic than acetic acid (CH3CO2H). Нас — ОН ОН H3C- ОН OH pKa = 15.5 pKa = 10.0 pk = 4.75 pk = 4.2arrow_forward
- Although p-hydroxybenzoic acid is less acidic than benzoic acid, o-hydroxybenzoic acid is slightly more acidic than benzoic acid. Explain this result. OH но -COOH -соон p-hydroxybenzoic acid o-hydroxybenzoic acidarrow_forwardPQ-27. What is the product of this reaction? (A) 0 OH a (B) (D) H₂ Ptarrow_forwardWhich is more acidic, p-methylphenol or phenol? why? Why is water more acidic than ethanol but slightly less acidic than methanol? Explain the acidity trend of alcohols: 1>2 > 3arrow_forward
- (b) Cortisone OH H2C CH -HO- H3C Oalcohol O carbon-carbon double bond Oester Oaldehyde Ocarbon-carbon triple bond Oether O amide Ocarboxylate anion Oketone Oamine O carboxylic acid O thiol (c) Prostaglandin PGE2 COOH Но OH Oalcohol O carbon-carbon double bond Oester Oaldehyde Ocarbon-carbon triple bond Oether Oketone O amide O carboxylate anion Oamine Ocarboxylic acid O thiolarrow_forwardH3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3arrow_forwardRank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.arrow_forward