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Interpretation:
Synthetic intermediates A and B have to be drawn.
Concept Introduction:
Conversion of alcohol into
Conversion of primary and secondary alcohols to Chloroalkane is thionyl chloride. The reaction is carried out in the presence of base such as pyridine or trimethylamine.
The reaction of an alcohol with thionyl chloride is the formation of an alkyl Chlorosulfite that converts hydroxide ion (poor leaving group) into Chlorosulfite (good leaving group). Nucleophilic displacement of this leaving group gives product.
Leaving group: Leaving group can be any groups or atoms that get detached from either neutral or charged organic compounds. The stability of the leaving group is to stabilize the electron density that results from heterolysis cleavage of bond.
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Chapter 10 Solutions
Organic Chemistry
- Draw the structural formula of the products formed when each alkene is treated with one equivalent of NBS in CH2Cl2 in the presence of light.arrow_forwardBoth 1,2-dihydronaphthalene and 1,4-dihydronaphthalene may be selectively hydrogenated to 1,2,3,4-tetrahydronaphthalene.One of these isomers has a heat of hydrogenation of 101 kJ/mol (24.1 kcal/mol), and the heat of hydrogenation of the other is 113 kJ/mol (27.1 kcal/mol). Match the heat of hydrogenation with the appropriate dihydronaphthalene.arrow_forwardSN2 reaction is an example of a nucleophilic substitution reaction. Imagine that 1-iodobutane reacts with 4-methylheptan-1-ol under basic conditions. Draw the structure of the two reactants.arrow_forward
- DRAW THE COMPOUNDS WITH THE FOLLOWING IUPAC NAMES...arrow_forwardTerpineol has 5 isomers. Write their structures and describe why chemically (optically) they receive those names. Number the carbons for a better description.arrow_forwardIn the chemical synthesis of DNA and RNA, hydroxyl groups are normally converted to triphenylmethyl (trityl) ethers to protect the hydroxyl group from reaction with other reagents. Triphenylmethyl ethers are stable to aqueous base but are rapidly cleaved in aqueous acid. (a) Why are triphenylmethyl ethers so readily hydrolyzed by aqueous acid? (b) How might the structure of the triphenylmethyl group be modified to increase or decrease its acid sensitivity?arrow_forward
- What products would result from the following processes? Write an equation for each reaction. a. 2-Methyl-2-butanol is subjected to controlled oxidation. b. 1-Propanol is heated to 140C in the presence of sulfuric acid. c. 3-Pentanol is subjected to controlled oxidation. d. 3-Pentanol is heated to 180C in the presence of sulfuric acid. e. 1-Hexanol is subjected to an excess of oxidizing agent.arrow_forwardAccount for the fact that treating propenoic acid (acrylic acid) with HCl gives only 3-chloropropanoic acid.arrow_forwardGive IUPAC names for the following compounds:arrow_forward
- 16-54 Several poisonous plants, including Atropa belladonna, contain the alkaloid atropine. The name “belladonna” (which means “beautiful lady”) probably comes from the fact that Roman women used extracts from this plant to make themselves more attractive. Atropine is widely used by ophthal mologists and optometrists to dilate the pupils for eye examination. Classify the amino group in atropine as primary, secondary, or tertiary. Locate all stereocenters in atropine. Account for the fact that atropine is almost insoluble in water (1 g in 455 mL of cold water) but atropine hydrogen sulfate is very soluble (1 g in 5 mL of cold water). Account for the fact that a dilute aqueous solution of atropine is basic (pH approximately 10.0).arrow_forwardGive IUPAC names for the following substances:arrow_forwardIdentify the most important aldehyde and ketone from Section 14.4 on the basis of amount used, and list at least one characteristic for each that contributes to its usefulness.arrow_forward
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