Concept explainers
(a)
Interpretation:
Major
Concept Introduction:
A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks the positive center, and removal of the good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.
(b)
Interpretation:
Major alkene product by the dehydration of 1-methylcyclohexanol needs to be identified:
Concept Introduction:
A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks the positive center, and removal of the good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.
(c)
Interpretation:
Major alkene product by the dehydration of 2-methyl cyclohexanol needs to be identified:
Concept Introduction:
A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.
(d)
Interpretation:
Major alkene product by the dehydration of 2,2-dimethylcyclohexanol needs to be identified:
Concept Introduction:
A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.
(e)
Interpretation:
Major alkene product by the dehydration of 1,2-cyclohexanediol needs to be identified:
Concept Introduction:
A dehydration reaction takes place after the removal of water molecule/s from the reactant molecule. In the mechanism of any organic reaction, negative charge always attacks on the positive center, and removal of good leaving group takes place. The stability of a leaving group depends on the stability of the molecule which can be shown by inductive, hyperconjugation or resonance effect.
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Chapter 22 Solutions
EBK A SMALL SCALE APPROACH TO ORGANIC L
- Aldehydes and ketones react with one molecule of an alcohol to form compounds called hemiacetals, in which there is one hydroxyl group and one ether-like group. Reaction of a hemiacetal with a second molecule of alcohol gives an acetal and a molecule of water. We study this reaction in Chapter 16. Draw structural formulas for the hemiacetal and acetal formed from these reagents. The stoichiometry of each reaction is given in the problem.arrow_forward1. Draw structures for the following molecules. 1,5-dihydroxypentan-3-one p-nitrobenzaldehyde (3S)-4-hydroxy-3-methylbutanal 3-phenylcyclohex-2-enonearrow_forward9. Give the structures of the alcohol and the aldehyde or ketone needed to prepare each of the following. H+ 80 H* -애 OH H* Одн OH hemi H* H+ to H* HO hemiarrow_forward
- Aldehydes and ketones react with thiols to yield thioacetals, just as they react with alcohols to yield acetals. Draw the structure of the third intermediate in this reaction. H* catalyst .SCH3 + 2 CH3SH SCH3arrow_forwardIdentify the alcohol reactant needed to produce each of the following compounds as the major product of an alcohol dehydration reaction. H,SO, Alcohol → CH3–CH=CH–CH3 180°C a. H,SO, Alcohol → CH,=CH-CH–CH3 180°C CH3 b. H,SO, Alcohol CH3-CH-CH2–0–CH,-CH–CH3 140°C ČH3 с. H,SO, Alcohol CH,=CH-CH,–CH3 180°C H,SO, Alcohol CH;-C=C-CH3 180°C CH3 CH3 e.arrow_forwardComplete the table below with all the missing information. Note: more than one reactant/reagent/product may be required in a row/column.arrow_forward
- name the alkene product obtained on dehydration of each of the following alcohols: 1-Butanol 2-Butanol 2-Methyl-2-propanol 2,3,3-Trimethyl-2-butanolarrow_forwardWhich of the following ketones would be the most soluble in water? (Hìnt: Remember the relation between the number of carbons in aldehydes and ketones and their solubility in water.) O CH3-CH2-CH2-CO-CH3 O CH3-CH2-CH2-CO-CH2-CH2-CH3 O CH3-CO-CH2-CH3 O CH3-CO-CH2-CH2-CH2-CH3arrow_forwardThe name of this organic compound. H- CH-COOH O 3,4-diketobutanoic acid 3-oxobutanal 3,4-dioxobutanoic acid 3-oxobutanoic acid The IUPAC name of this compound. OCH, CHO 2-methoxycyclohexanecarbaldehyde cis-6-methoxycyclohexanecarbaldehyde trans-6-methoxycyclohexanecarbaldehyde trans-2-methoxycyclohexanecarbaldehydearrow_forward
- Classify the following compounds as ketals, hemiketals, acetals, hemiacetals, or thioketals, as appropriatearrow_forwardExplain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardAlkenes can be converted to alcohols by reaction with mercuric acetate to form a ß-hydroxyalkylmercury(II) acetate compound, a reaction called oxymercuration. Subsequent reduction with NaBH reduces the C-Hg bond to a C-H bond, forming the alkyl alcohol, a reaction called demercuration. Draw the structure of the Hg-containing compound and the final alcohol product formed in the reaction sequence. CH3 Hg(OOCCH3)2 NaBH4 HO™ Oxymercuration product Demercuration Product H₂O, THF Draw the alcohol product of demercuration. Draw the neutral product of oxymercuration. Omit byproducts. OH Hg Incorrectarrow_forward
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