1 Structure And Bonding 2 Acids And Bases 3 Introduction To Organic Molecules And Functional Groups 4 Alkanes 5 Stereochemistry 6 Understanding Organic Reactions 7 Alkyl Halides And Nucleophilic Substitution 8 Alkyl Halides And Elimination Reactions 9 Alcohols, Ethers, And Related Compounds 10 Alkenes 11 Alkynes 12 Oxidation And Reduction 13 Mass Spectrometry And Infrared Spectroscopy 14 Nuclear Magnetic Resonance Spectroscopy 15 Radical Reactions 16 Conjugation, Resonance, And Dienes 17 Benzene And Aromatic Compounds 18 Reactions Of Aromatic Compounds 19 Carboxylic Acids And The Acidity Of The O-h Bond 20 Introduction To Carbonyl Chemistry; Organometallic Reagents; Oxidation And Reduction 21 Aldehydes And Ketones-nucleophilic Addition 22 Carboxylic Acids And Their Derivatives-nucleophilic Acyl Substitution 23 Substitution Reactions Of Carbonyl Compounds At The α Carbon 24 Carbonyl Condensation Reactions 25 Amines 26 Carbon–carbon Bond-forming Reactions In Organic Synthesis 27 Pericyclic Reactions 28 Carbohydrates 29 Amino Acids And Proteins 30 Synthetic Polymers 31 Lipids expand_more
Chapter Questions expand_more
Problem 21.1P: Rank the following compounds in order of increasing reactivity towards nucleophilic attack.
Problem 21.2P Problem 21.3P: Give the IUPAC name for each aldehyde. Problem 21.4P Problem 21.5P: Give the IUPAC name for each ketone. Problem 21.6P Problem 21.7P Problem 21.8P: The boiling point of is significantly higher than the boiling point of diethyl ether , even though... Problem 21.9P: Which carbonyl group in each pair absorbs at a higher frequency?
Problem 21.10P: Problem 21.10 Draw the structure of all constitutional isomers that contain a ketone and have... Problem 21.11P Problem 21.12P Problem 21.13P Problem 21.14P Problem 21.15P: Problem 21.15 Draw the product of each reaction.
b.
Problem 21.16P Problem 21.17P: Problem 21.17 Draw the products of the following Wittig reactions.
b.
Problem 21.18P: Problem 21.18 Outline a synthesis of each Wittig reagent from and an alkyl halide.
b. c.
Problem 21.19P: Problem 21.19 Draw the products (including stereoisomers) formed when benzaldehyde is treated with... Problem 21.20P: Problem 21.20 What starting materials are needed to prepare each alkene by a Wittig reaction? When... Problem 21.21P Problem 21.22P: Problem 21.22 The product formed when reacts with given carbonyl compound in presence of mild... Problem 21.23P Problem 21.24P Problem 21.25P Problem 21.26P Problem 21.27P Problem 21.28P: Problem 21.28 Draw a stepwise mechanism for the following reaction.
Problem 21.29P: Problem 21.29 Draw the products of each reaction.
b.
Problem 21.30P: Problem 21.30 Label each compound as an acetal, a hemiacetal, or an ether.
b. c. d.
Problem 21.31P: Problem 21.31 Draw a stepwise mechanism for the following reaction.
Problem 21.32P: Problem 21.32 Draw the products of each reaction.
b.
Problem 21.33P: Problem 21.33 Safrole is a naturally occurring acetal isolated from sassafras plants. Once used as a... Problem 21.34P Problem 21.35P: Problem 21.35 How would you use a protecting group to carry out the following transformation?
Problem 21.36P Problem 21.37P: Problem 21.37 Two naturally occurring compounds that contain stable cyclic hemiacetals and acetals... Problem 21.38P: Problem 21.38 Draw the products of each reaction.
b.
Problem 21.39P Problem 21.40P: Problem 21.40 (a) Give the IUPAC name for A and B. (b) Draw the product formed when A or B is... Problem 21.41P: 21.41 Rank the following compounds in order of increasing reactivity in nucleophilic addition.
Problem 21.42P Problem 21.43P: 21.43 Give the IUPAC name for each compound.
a. c. e.
b. d. f.
Problem 21.44P: 21.44 Give the structure corresponding to each name.
Problem 21.45P Problem 21.46P: 21.46 Draw the products of each reaction.
a. e.
b. f.
c. g.
d. h.
Problem 21.47P Problem 21.48P: 21.48 Draw all stereoisomers formed in each reaction.
a. c.
b. d.
Problem 21.49P Problem 21.50P: What products are formed when each acetal is hydrolyzed with aqueous acid?
a. b.
Problem 21.51P Problem 21.52P Problem 21.53P: Which compound forms the higher concentration of hydrate at equilibrium,
or ? Explain your... Problem 21.54P Problem 21.55P Problem 21.56P Problem 21.57P Problem 21.58P: Devise a synthesis of each alkene using a Wittig reaction to form the double bond. You may use... Problem 21.59P: Devise a synthesis of each compound from cyclohexene and organic alcohols. You may use any other... Problem 21.60P Problem 21.61P: Devise a synthesis of each compound from ethanol (CH3CH2OH) as the only source of carbon atoms. You... Problem 21.62P Problem 21.63P Problem 21.64P: 21.64 Draw a stepwise mechanism for the following reaction.
Problem 21.65P: 21.65 Draw a stepwise mechanism f or the following reaction, a key step in the synthesis of the... Problem 21.66P Problem 21.67P: 21.67 Draw a stepwise mechanism for each reaction.
a.
b.
Problem 21.68P: 21.68 Draw a stepwise mechanism for the following reaction that converts a dicarbonyl compound to a... Problem 21.69P Problem 21.70P Problem 21.71P Problem 21.72P Problem 21.73P: 21.73 Although the carbonyl absorption of cyclic ketones generally shifts to higher wavenumber with... Problem 21.74P: 21.74 Use the and data to determine the structure of each compound.
Compound A Molecular... Problem 21.75P: 21.75 A solution of acetone in ethanol in the presence of a trace of acid was allowed to stand f or... Problem 21.76P: Compounds A and B have molecular formula . Identify their structures from the and spectra given.
Problem 21.77P: 21.77 An unknown compound C of molecular formula exhibits a strong absorption in its spectrum at ... Problem 21.78P: 21.78 An unknown compound D exhibits a strong absorption in its spectrum at . The mass spectrum
... Problem 21.79P Problem 21.80P: -D-Glucose, a hemiacetal, can be converted to a mixture of acetals on treatment with CH3OH in the... Problem 21.81P: 21.81 Draw a stepwise mechanism for the following reaction.
Problem 21.82P Problem 21.83P: 21.83 Draw a stepwise mechanism f or the following reaction.
Problem 21.84P Problem 21.85P Problem 21.86P: 21.86 Draw stepwise mechanism for the following reaction, a key step in the synthesis of
conivaptan... format_list_bulleted