ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Textbook Question
Chapter 11, Problem 11.13P
(a) Draw two different enol tautomers of
constitutional isomers that are not tautomers, but contain a
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[10]
10]
Q1. Do the following conversions as directed. Write the complete reaction equation.
(a) Benzaldehyde to Benzoic Acid.
(b) Propanal to 1-propanal
(c) Cyclohexanone to Cyclohexanol
(d) Acetaldehyde to Ethyl alcohol
(e) Acetone to Iso-propyl alcohol
4
But-2-enal, CH₂CH=CHCHO, is a pale yellow, flammable liquid with an irritating odour.
(a) But-2-enal exists as two stereoisomers.
Draw skeletal formulae to show the structure of the two stereoisomers of but-2-enal.
(b) (i) Describe a simple chemical test that would show that but-2-enal is an aldehyde.
(ii) Explain why this test gives a different result with aldehydes than it does with keton
(c) But-2-enal also reacts with sodium borohydride, NaBH4.
(i) Identify the organic compound formed in this reaction.
(ii) State the type of chemical reaction occurring.
(d) Precautions must be taken to prevent but-2-enal catching fire.
Construct a balanced equation for the complete combustion of but-2-enal, C₂HO.
Draw the following compound.(2E)-but-2-enal
(3Z)-4-hydroxypent-3-enoic acid
Chapter 11 Solutions
ORGANIC CHEMISTRY
Ch. 11 - Problem 11.1 Neopheliosyne B is a novel acetylenic...Ch. 11 - Give the IUPAC name for each compound.Ch. 11 - Give the structures corresponding to each of the...Ch. 11 - Prob. 11.4PCh. 11 - Prob. 11.5PCh. 11 - Which bases can deprotonate acetylene? The pKa...Ch. 11 - Draw the organic products formed when each alkyne...Ch. 11 - Draw additional resonance structures for each...Ch. 11 - Problem 11.9 Draw the products formed when is...Ch. 11 - Explain the following result. Although alkenes...
Ch. 11 - Problem 11.11 Draw the keto tautomer of each...Ch. 11 - Prob. 11.12PCh. 11 - a Draw two different enol tautomers of...Ch. 11 - Prob. 11.14PCh. 11 - Problem 11.15 Draw the organic products formed in...Ch. 11 - Problem 11.16 What acetylide anion and alkyl...Ch. 11 - Problem. 11.17 Show how , and can be used to...Ch. 11 - Prob. 11.18PCh. 11 - Draw the products of each reaction. a. b.Ch. 11 - Prob. 11.20PCh. 11 - Problem 11.21 Use retrosynthetic analysis to show...Ch. 11 - Prob. 11.22PCh. 11 - Give the IUPAC name for each compound. a. b.Ch. 11 - Prob. 11.24PCh. 11 - 11.25 Answer the following questions about...Ch. 11 - 11.26 Give the IUPAC name for each alkyne.
a. ...Ch. 11 - Prob. 11.27PCh. 11 - Which of the following pairs of compounds...Ch. 11 - Prob. 11.29PCh. 11 - 11.30 How is each compound related to A? Choose...Ch. 11 - Prob. 11.31PCh. 11 - Prob. 11.32PCh. 11 - 11.33 Draw the products formed when is treated...Ch. 11 - What reagents are needed to convert (CH3CH2)3CCCH...Ch. 11 - Prob. 11.35PCh. 11 - 11.36 What alkynes give each of the following...Ch. 11 - 11.37 What alkyne gives each compound as the only...Ch. 11 - 11.38 Draw the organic products formed in each...Ch. 11 - 11.39 Draw the structure of compounds A-E in the...Ch. 11 - Prob. 11.40PCh. 11 - Prob. 11.41PCh. 11 - 11.42 What reactions are needed to convert alcohol...Ch. 11 - Prob. 11.43PCh. 11 - Prob. 11.44PCh. 11 - 11.45 Explain the following statement. Although ...Ch. 11 - 11.46 Tautomerization in base resembles...Ch. 11 - 11.47 Draw a stepwise mechanism for each...Ch. 11 - Prob. 11.48PCh. 11 - Prob. 11.49PCh. 11 - 11.50 What acetylide anion and alkyl halide are...Ch. 11 - 11.51 Synthesize each compound from acetylene. You...Ch. 11 - 11.52 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.53PCh. 11 - Prob. 11.54PCh. 11 - 11.55 Devise a synthesis of the ketone, , from ...Ch. 11 - 11.56 Devise a synthesis of each compound using ...Ch. 11 - Prob. 11.57PCh. 11 - Prob. 11.58PCh. 11 - 11.59 N-Chlorosuccinimide (NCS) serves as a source...Ch. 11 - 11.60 Draw a stepwise mechanism for the following...Ch. 11 - 11.61 Draw a stepwise mechanism for the following...Ch. 11 - Prob. 11.62PCh. 11 - 11.63 Write a stepwise mechanism for each of the...Ch. 11 - Prob. 11.64PCh. 11 - 11.65 Explain why an optically active solution of ...
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