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- A compound with formula C7H12O is treated with sodium borohydride in methanol to yield 2,2-dimethylcylopentanol. Write a reaction scheme showing the structures of the reactant, the reagents, and the product. Will the product be optically active? Explain.Citronellol ((3R)-3,7-dimethyloct-6-en-1-ol, C10H20O) is an organic fragrance found in the oil extracted from lemon grass. a) Name the two functional groups present in the molecule. b) When a few drops of bromine dissolved in hexane is added to a sample of citronellol the brown colour of the bromine rapidly disappears. i. What type of chemical reaction has occurred? ii. Draw the structure of the product formed. iii. Name the product. c) The product formed when citronellol is heated with a mixture of potassium dichromate and sulfuric acid gives a yellow/orange precipitate when shaken with Brady’s reagent (2,4-dinitrophenylhydrazine). It also shows a positive result with Fehling’s solution. i. What type of chemical reaction has occurred ? ii. What type of functional group is present in the product? d) Explain the type of stereoisomerism which may occur in citronellol.4. What are the products from the following reaction? H3O+ کا
- 4.) HX is used as a reagent in the reaction below. „NH2 он + HX + :NEN: + A. What functional-group transformation occurs in this reaction?Reaction of (CH3)3CH with Cl2 forms two products: (CH3)2CHCH2Cl (63%) and (CH3)3CCl (37%). Why is the major product formed by cleavage of the stronger 1° C–H bond?Organometallic reagents such as sodium acetylide undergo an addition reaction with ketones, giving alcohols: он 1. Na+ -:CECH 2. H3O* .C-C=CH How might you use this reaction to prepare 2-methyl-1,3-butadiene?
- When 2-pentene is treated with Cl, in methanol, three products are formed. Account for the formation of each product (you need not explain their relative percentages). CI OCH3 H,CO CI CI CI Cle CH;CHCHCH,CH, + CH;CHCHCH,CH3 + CH,CHČHCH,CH, CH;OH CH;CH=CHCH,CH, 50% 35% 15%Compounds A and B are isomers of the molecular formula CyH19Br. Both yield the same alkene Cin an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?║? What is the structure of the alkene that would produce CH3─ C─ CH2CH3 and H─C─H when treated with ozone and then with zinc and acetic acid? ║ O
- Draw structures for compounds A through D. 1. NaOH, H2O A 2. H,0°A 1. NaOEt, EtOH (a) Ethyl acetoacetate → B 2. 1-Chloro-4-methylpentane Same as above 1. NaOH, H2O D 1. NaOC(CH3)3, (CH3);COH (b) A 2. 1-Chloropropane 2. H,0ºAAlcohols undergo an oxidation reaction to yield carbonyl compounds on treatment with CrO3. For example, 2-tert-butylcyclohexanol gives 2-tert-butylcyclohexanone. If axial OH groups are generally more reactive than their equatorial isomers, which do you think reacts faster, the cis isomer of 2-tert-butylcyclohexanol or the trans isomer? Explain.Draw structures of compounds that fit the following descriptions: a) An , unsaturated ketone, C9H8O b) An diketone c) An aromatic ketone, C9H10O d) A diene aldehyde, C7H8O