Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Textbook Question
Chapter 9.1, Problem 1P
Draw the structures of straight-chain alcohols that have from one to six carbons with an OH group at the end of the chain, and then give each of them a common name and a systematic name.
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Stingless bees use complex systems to communicate. One aspect of this communication is chemical: the bees produce 2-nonanol, 2-heptanol, and 2-undecanol in their mouthparts (mandibles) to direct other bees to pollen sources. Draw the condensed structure of each of these alcohols. Classify each as a primary, secondary, or tertiary alcohol.
Which is NOT a physical property of alcohols or phenols?
O Phenols are generally only slightly soluble in water.
O The hydroxyl group of an alcohol is nonpolar.
The solubilities of normal primary alcohols in water
decrease with increasing molecular weight.
Boiling points of normal primary alcohols increase
with increasing molecular weight.
Using the relationship between the structure and the boiling point. Obtain a table for the listed chemicals below showing how the boiling point will be different with (1) the different chemical structures, (2) with different functional groups.
Boiling Point and Functionalized Compounds:
Chemical:
Cyclohexanol
Cyclohexanone
Cyclohexene
Benzaldehyde
Benzyl alcohol
Chapter 9 Solutions
Essential Organic Chemistry, Global Edition
Ch. 9.1 - Draw the structures of straight-chain alcohols...Ch. 9.1 - Prob. 2PCh. 9.1 - Prob. 3PCh. 9.2 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 9.2 - Prob. 5PCh. 9.2 - The observed relative reactivities of primary,...Ch. 9.4 - Which of the following alcohols would dehydrate...Ch. 9.4 - Prob. 10PCh. 9.4 - Prob. 11PCh. 9.4 - Prob. 12P
Ch. 9.4 - Prob. 13PCh. 9.5 - What product will be obtained from the reaction of...Ch. 9.5 - Prob. 15PCh. 9.6 - a. What is each ethers systematic name? 1....Ch. 9.8 - Draw the structure of the following: a....Ch. 9.8 - Prob. 20PCh. 9.8 - Would you expect the reactivity of a five-membered...Ch. 9.9 - Explain why the two arene oxides in Problem 22...Ch. 9.9 - Which compound is more likely to be...Ch. 9.11 - The following three nitrogen mustards were studied...Ch. 9 - What are the common and systematic names of the...Ch. 9 - Prob. 28PCh. 9 - Prob. 29PCh. 9 - Prob. 30PCh. 9 - Prob. 31PCh. 9 - What is the major product obtained from the...Ch. 9 - Draw structures for the following: a....Ch. 9 - Prob. 34PCh. 9 - Prob. 35PCh. 9 - Prob. 36PCh. 9 - Prob. 37PCh. 9 - Ethylene oxide reacts readily with HO.because of...Ch. 9 - Propose a mechanism for each of the following...Ch. 9 - Which of the following ethers would be obtained in...Ch. 9 - Show how each of the following syntheses could be...Ch. 9 - Prob. 42PCh. 9 - Prob. 43PCh. 9 - Prob. 44PCh. 9 - Propose a mechanism for each of the following...Ch. 9 - a. Propose a mechanism for the following reaction:...Ch. 9 - Three arene oxides can be obtained from...Ch. 9 - Prob. 48PCh. 9 - The following reaction takes place several times...Ch. 9 - Show how each of the following compounds could be...Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - Propose a mechanism for the following reaction:Ch. 9 - What alkenes would you expect to be obtained from...Ch. 9 - Triethylenemelamine (TEM) is an antitumor agent....Ch. 9 - When a diol that has OH groups on adjacent carbons...Ch. 9 - What product is obtained when...Ch. 9 - Prob. 58P
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- Draw the structures of a homologous series of alcohols that have from one to six carbons and give each of them a common name and a systematic name.arrow_forwardDescribe chemical properties of alcohols (intermolecular dehydration, intramolecular dehydration).arrow_forwardGive the common name for NN OH T CH3-CH₂-C-N-CH₂-CH3 Spell out the common name of the compound. Give the IUPAC name for 0 CH₂ || CH₂-C-N-CH₂-CH₂-CH₂, Spell out the IUPAC name of the compound. diethylamine Draw all missing reactants and/or products in the appropriate boxes by placing atoms on the canvas and connecting them with bonds. Add charges where needed. HE CONT HOarrow_forward
- Give the IUPAC name of the alcohol that fits each of the following descriptions. a. Moistening agent in many cosmetics b. Major ingredient in environmentally friendly antifreeze formulations c. Industrially produced from CO and H2 d. Often produced via a fermentation processarrow_forwardClassify the following alcohols as primary, secondary, or tertiary: a. b.CH3CH2CH2CH2OH c.arrow_forwardDetermine the maximum number of hydrogen bonds that can form between an ethanol molecule and a. other ethanol molecules b. water molecules c. methanol molecules d. 1-propanol moleculesarrow_forward
- What functional group distinguishes each of the following hydrocarbon derivatives? a. halohydrocarbons b. alcohols c. ethers d. aldehydes e. ketones f. carboxylic acids g. esters h. amines Give examples of each functional group. What prefix or suffix is used to name each functional group? What are the bond angles in each? Describe the bonding in each functional group. What is the difference between a primary, secondary, and tertiary alcohol? For the functional groups in ah, when is a number required to indicate the position of the functional group? Carboxylic acids are often written as RCOOH. What does COOH indicate and what does R indicate? Aldehydes are sometimes written as RCHO. What does CHO indicate?arrow_forwardDraw the compound (Skeletal form) Compound Boiling Point Melting Point Pentane 1-Butanol 1-hexanol Нехуlamine Cyclohexane Cyclohexanethiol Cyclohexanolarrow_forwardWrite the skeletal structures of propanal, acetone and cyclohexanone. What is the major intermolecular force (IMF) found in them? Based on their major intermolecular force and molecular weight, what can you predict on their solubility in water? Chemical Name Skeletal Structures Major IMF Solubility in water Propanal Acetone Cyclohexanonearrow_forward
- 1. Write the skeletal structures of propanal, acetone and cyclohexanone. What is the major intermolecular force (IMF) found in them? Based on their major intermolecular force and molecular weight, what can you predict on their solubility in water? Chemical Name Skeletal Structures Major IMF Solubility in water Propanal Acetone Cyclohexanone 2. What is the purpose of Tollens’ test (Part B)? What is the evidence of a positive result? 3. What is the purpose of oxidation test (Part C)? What is the evidence of a positive result?arrow_forwardDraw the condensed structural formula or skeletal formula, if cyclic, for the alcohol needed to give each of the following oxidation products: || а. Н—С—Н b.arrow_forwardDraw structures for the four constitutional isomers of molecular formula C4H10O that contain an OH group. Give the IUPAC name for each alcohol.arrow_forward
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