Introduction to General, Organic and Biochemistry
11th Edition
ISBN: 9781285869759
Author: Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher: Cengage Learning
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Chapter 17.4, Problem 17.6P
Problem 17-6
Show the reaction of benzaldehyde with one molecule of methanol to form a hemiacetal and then with a second molecule of methanol to form an acetal.
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PROBLEM 18-28(a) Propose a mechanism for the acid-catalyzed reaction of cyclohexanone with ethyleneglycol to give cyclohexanone ethylene acetal.(b) Propose a mechanism for the acid-catalyzed hydrolysis of cyclohexanone ethylene acetal.(c) Compare the mechanisms you drew in parts (a) and (b). How similar are these mechanisms,comparing them in reverse order?
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A common ketone starting material is
shown below. Predict the major product
for each reaction based on the reagents
given. Ignore any inorganic byproducts.
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=
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H3O+
NaCN, HCI
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1. PhCCNa
2. H3O+
NH2NH2,
TSOH
PROBLEM 18-9Show how the following transformations may be accomplished in good yield. You mayuse any additional reagents that are needed. benzoic acid S phenyl cyclopentyl ketone
Chapter 17 Solutions
Introduction to General, Organic and Biochemistry
Ch. 17.2 - Problem 17-1 Wrtie the IUPAC name for each...Ch. 17.2 - Prob. 17.2PCh. 17.2 - Prob. 17.3PCh. 17.4 - Prob. 17.4PCh. 17.4 - Prob. 17.5PCh. 17.4 - Problem 17-6 Show the reaction of benzaldehyde...Ch. 17.4 - Problem 17-7 Identify all hemiacetals and acetals...Ch. 17.5 - Prob. 17.8PCh. 17 - 17-9 Answer true or false. (a) The one aldehyde...Ch. 17 - Prob. 17.10P
Ch. 17 - 17-11 What is the difference in structure between...Ch. 17 - 17-12 Is it possible for the carbon atom of a...Ch. 17 - 17-13 Which compounds contain carbonyl groups?Ch. 17 - 17-14 Following are structural formulas for two...Ch. 17 - 17-15 Draw structural formulas for the four...Ch. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - 17-18 Draw structural formulas for these ketones....Ch. 17 - 17-19 Write the JUPAC names for these compounds.Ch. 17 - Prob. 17.20PCh. 17 - 17-2 1 Explain why each name is incorrect. Write...Ch. 17 - Prob. 17.22PCh. 17 - Prob. 17.23PCh. 17 - 17-24 In each pair of compounds, select the one...Ch. 17 - Prob. 17.25PCh. 17 - 17-26 Account for the fact that acetone has a...Ch. 17 - 17-27 Pentane, 1-butanol, and butanal all have...Ch. 17 - 17-28 Show how acetaldehyde can form hydrogen...Ch. 17 - 17-29 Why can’t two molecules of acetone form a...Ch. 17 - 17-30 Answer true or false. (a) The reduction of...Ch. 17 - 17-3 1 Draw a structural formula for the principal...Ch. 17 - Prob. 17.32PCh. 17 - 17-33 What simple chemical test could you use to...Ch. 17 - 17-34 Explain why liquid aldehydes are often...Ch. 17 - 17-35 Suppose that you take a bottle of...Ch. 17 - 17-36 Explain why the reduction of an aldehyde...Ch. 17 - Prob. 17.37PCh. 17 - Prob. 17.38PCh. 17 - Prob. 17.39PCh. 17 - Prob. 17.40PCh. 17 - Prob. 17.41PCh. 17 - Prob. 17.42PCh. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Prob. 17.46PCh. 17 - 17-47 What is the characteristic structural...Ch. 17 - Prob. 17.48PCh. 17 - Prob. 17.49PCh. 17 - Prob. 17.50PCh. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - Prob. 17.53PCh. 17 - 17-54 Following is the structure of...Ch. 17 - Prob. 17.55PCh. 17 - Prob. 17.56PCh. 17 - Prob. 17.57PCh. 17 - Prob. 17.58PCh. 17 - Prob. 17.59PCh. 17 - 17-60 1-Propanol can be prepared by the reduction...Ch. 17 - Prob. 17.61PCh. 17 - 17-62 Show how to bring about these conversions....Ch. 17 - Prob. 17.63PCh. 17 - Prob. 17.64PCh. 17 - Prob. 17.65PCh. 17 - Prob. 17.66PCh. 17 - 17-67 Draw structural formulas for these...Ch. 17 - Prob. 17.68PCh. 17 - 17-69 Propanal (bp 49°C) and 1-propanol (bp 97°C)...Ch. 17 - 17-70 What simple chemical test could you use to...Ch. 17 - Prob. 17.71PCh. 17 - 17-72 The following molecule is an enediol; each...Ch. 17 - 17-73 Alcohols can be prepared by the...Ch. 17 - 17-74 Glucose, C6H12O6, contains an aldehyde group...Ch. 17 - Prob. 17.75PCh. 17 - Prob. 17.76PCh. 17 - Prob. 17.77PCh. 17 - 17-78 Complete the following equation for these...Ch. 17 - 17-79 Write an equation for each conversion. (a)...
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- PROBLEM 10-15 Show how you would synthesize each tertiary alcohol by adding an appropriate Grignard reagent to a ketone. (a) 3-phenylhexan-3-ol (3 ways) (b) Ph3COH (c) 1-ethylcyclopentanol (d) 2-cyclopentylpentan-2-olarrow_forwardPROBLEM 20-1Draw the structures of the following carboxylic acids. trans-2-methylcyclohexanecarboxylic acidarrow_forwardProblem Three a) Identify the following as nucleophile or electrophile: iii) C,H,CHO vi) HOC₂H₂ i) C,H5NH, iv) (C$Hs)₂CO ii) (C₂Hs)3N v) (C₂H5)₂CH+ viii) CH,SH vii) CN ix) CH₂CH₂CH₂CH₂ Br b) i) Draw the curly arrow mechanism for the reaction between v) and vii) x) (CH3)3CBr ii) of the two C atoms involved do any change their hybridisation? If so, how?arrow_forward
- only typed solutionarrow_forwardProblem 17-7 Identify all hemiacetals and acetals in the following structures and tell whether each is formed from an aldehyde or a ketone. OH (a) (b) CH3OCH2CH2OCH3 (c)arrow_forwardC. Problem 16-71 How would you synthesize the following compounds from benzene? Assume that the ortho and para isomers can be separated. You don't need to show mechanisms, only reagents. i) CH3 AVC3 1 2 Brz Al Brz 2 HNO3, H₂504 02N Brarrow_forward
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