Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 9, Problem 26P
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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.
In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a
ketone (C5H100) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst.
The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric
acid (HCI) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this
series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt
please provide valuable answer
The acid-catalyzed dehydration of 2,3-dimethyl-3-pentanol yields three alkene products. What are the names of the three alkenes?
Which of the three alkenes is the major product?
Chapter 9 Solutions
Organic Chemistry - Standalone book
Ch. 9.1 - Prob. 1PCh. 9.2 - Prob. 2PCh. 9.4 - How do bond distances and bond strengths change...Ch. 9.5 - Complete each of the following equations to show...Ch. 9.6 - Prob. 5PCh. 9.6 - Which of the alkynes of molecular formula C5H8 can...Ch. 9.7 - Give the structures of three isomeric dibromides...Ch. 9.7 - Prob. 8PCh. 9.9 - Write a series of equations showing how you could...Ch. 9.9 - Write a series of equations showing how to prepare...
Ch. 9.10 - Prob. 11PCh. 9.11 - Give the structure of the enol formed by hydration...Ch. 9.11 - Prob. 13PCh. 9.13 - Prob. 14PCh. 9.14 - Prob. 15PCh. 9 - Provide the IUPAC name for each of the following...Ch. 9 - Prob. 17PCh. 9 - All compounds in Problem 9.17 are isomers except...Ch. 9 - Prob. 19PCh. 9 - Write structural formulas for all the alkynes of...Ch. 9 - Prob. 21PCh. 9 - Prob. 22PCh. 9 - The alkane formed by hydrogenation of...Ch. 9 - Write the structure of the major organic product...Ch. 9 - Write the structure of the major organic product...Ch. 9 - When 2-heptyne was treated with aqueous sulfuric...Ch. 9 - Prob. 27PCh. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Show by writing appropriate chemical equations how...Ch. 9 - Diphenylacetylene can be synthesized by the double...Ch. 9 - (Z)-9-tricosene [ (Z)-CH3(CH2)7CH=CH(CH2)12CH3 ]...Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Alkynes undergo hydroboration to give...Ch. 9 - Prob. 38DSPCh. 9 - Prob. 39DSPCh. 9 - Prob. 40DSPCh. 9 - Prob. 41DSPCh. 9 - Thinking Mechanistically About Alkynes The...
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- Compounds A and B are isomers of the molecular formula C9H19Br. Both yield the same alkene C in an elimination reaction. Hydrogenation of C yields the product 2,3,3,4 tetramethyl pentane. What are the structures of A, B, and C?arrow_forwardDraw the organic product formed when the followingcompounds undergo a substitution reaction: (a) acetic acid and1-hexanol; (b) propanoic acid and dimethylamine; (c) ethanoicacid and diethylamine.arrow_forward1) The acid-catalyzed dehydration of 2-methyl-2-butanol yields two alkene products, what are the names of the two alkenes? 2) which of the two alkenes is the major product?arrow_forward
- Draw the structures of the following molecules: (a) Biacetyl, C4H6O2, a substance with the aroma of butter; it contains no rings or carbon-carbon multiple bonds. (b) Ethylenimine, C2H5N, a substance used in the synthesis of melamine polymers; it contains no multiple bonds. (c) Glycerol, C3H8O3, a substance isolated from fat and used in cosmetics; it has an -OH group on each carbon.arrow_forwardWhen the conjugate acid of aniline, C6H5NH3+, reacts with the acetate ion, the following reaction takes place: C6H5NH3+(aq)+CH3COO(aq)C6H5NH2(aq)+CH3COOH(aq) If Kafor C6H5NH3+ is 1.35105 and Kafor CH3COOH is 1.86105 , what is K for the reaction?arrow_forwardA 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.arrow_forward
- Diazomethane, CH2N2, is used in the organic chemistry laboratory despite its danger because it produces very high yields and is selective for reaction with carboxylic acids. Write the products of the following reactions.arrow_forwardThe following chemical reaction is used to synthesize a flavouring agent that has an aroma similar to bananas. H₂SO4(aq) CH3COOH(1) + CH₂(CH₂)₂OH(1) I || Identify the type of reaction that is represented by this synthesis. Select one: O hydrogenation O esterification O addition O substitution O elimination Identify the functional group and the IUPAC name for each of the three compounds in the reaction below: H₂SO4(aq) I Compound Functional Group IUPAC Name II CH₂COOH(1) + CH₂(CH₂)₂OH(1) I || III CH3COO(CH₂)₂CH₂(1) + H₂O(1) III IV ◆ → ◆ CH3COO(CH₂)₂CH₂(1) + H₂O(1) IV ||| ◆ ◆arrow_forwardWrite the reagent or draw structures of the starting material or organic product(s) in the following reactions. If more than one product is formed, identify the major product where possible. (a) (b) HO OH OH H2SO4 ? Cl₂ ? FeCl3arrow_forward
- What happens when (i) chlorobenzene is treated with Cl2/FeCl3,(ii) ethyl chloride is treated with AgNO2, and(iii) 2-bromopentane is treated with alcoholic KOH?arrow_forwardIn an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H10O) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answerarrow_forwardDraw the following structures: a) N-cyclopropyl-3-methylhexanamide b) phenylpropanoate c) 3-chloro-2-isopropoxynonanearrow_forward
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