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 Lipids 31 Synthetic Polymers expand_more
Chapter Questions expand_more
Problem 4.1P Problem 4.2P Problem 4.3P: (a) Classify the carbon atoms in each compound as ,, or . (b) Classify the hydrogen atoms in each... Problem 4.4P: Problem 3.3 Classify a carbon atom by the number of carbons to which it is bonded can also be
done... Problem 4.5P: Problem 4.3 Draw the five constitutional isomers having molecular formula C6H14.
Problem 4.6P Problem 4.7P Problem 4.8P: Draw the five constitutional isomers that have molecular formula C5H10 and contain one ring. Problem 4.9P: Give the IUPAC name for each compound. a. c. b. d. Problem 4.10P: Give the IUPAC name for each compound. a. (CH3)3CCH2CH(CH2CH3)2 b. CH3(CH2)3CH(CH2CH2CH3)CH(CH3)2 c.... Problem 4.11P: Problem 4.9 Give the structure corresponding to each IUPAC name.
Problem 4.12P Problem 4.13P: Give the IUPAC name for each compound. Problem 4.14P: Give the structure corresponding to each IUPAC name. a. 1, 2-dimethylcyclobutane b. 1, 1,... Problem 4.15P: Arrange the following compounds in order of increasing boiling point. Problem 4.16P: Problem 4.14 Draw the staggered and eclipsed conformations that result from rotation around the CC... Problem 4.17P Problem 4.18P: a.Draw the three staggered and three eclipsed conformations that result from rotation around the... Problem 4.19P: Problem 4.19 Consider rotation around the carbon-carbon bond in
.
a. Using Newman projections,... Problem 4.20P: Calculate the destabilization present in each eclipsed conformation. Problem 4.21P: Problem 4.21 Classify the ring carbons as up or down . Identify the bonds highlighted in bold as... Problem 4.22P: Draw a second chair conformation for each cyclohexane. Then decide which conformation is present in... Problem 4.23P Problem 4.24P: Problem 4.25 Draw the structure for each compound using wedges and dashed wedges.
Problem 4.25P: For cis-1, 3-diethylcyclobutane, draw a a stereoisomer; b a constitutional isomer. Problem 4.26P Problem 4.27P: Problem 4.28 Consider .
Draw structures f or the cis and trans isomers using a hexagon for the... Problem 4.28P: Problem 4.29 Draw a chair conformation of cyclohexane with one group and
one group that fits each... Problem 4.29P Problem 4.30P: Draw the products of each combustion reaction. Problem 4.31P: Explain why beeswax is insoluble in H2O, slightly soluble in ethanol (CH3CH2OH), and soluble in... Problem 4.32P Problem 4.33P: Name each alkane using the ball-and-stick model, and classify each carbon as 1,2,3,or4. Problem 4.34P: Consider the substituted cyclohexane shown in the ball-and-stick model. a.Label the substituents on... Problem 4.35P Problem 4.36P: 3.31 For each alkane: (a) classify each carbon atoms as , , or .(b) classify each
hydrogen atom as... Problem 4.37P Problem 4.38P Problem 4.39P: Give the IUPAC name for each compound. a. h.k. b.l. c. CH3CH2CH2C(CH3)2C(CH3)2CH2CH3 i.m. d.... Problem 4.40P: 4.39 Give the structure and IUPAC name for each of the nine isomers having molecular formula that... Problem 4.41P:
4.40 Draw the structure corresponding to each IUPAC name.
a.
b.
c.
d. cyclobutylcycloheptane
e.... Problem 4.42P Problem 4.43P Problem 4.44P: 4.42 Give the IUPAC name for each compound.
a. b. c.
Problem 4.45P Problem 4.46P Problem 4.47P: 4.45 Which conformation in each pair is higher in energy? Calculate the energy difference between... Problem 4.48P: Considering rotation around the bond highlighted in red in each compound, draw Newman projections... Problem 4.49P Problem 4.50P Problem 4.51P: 4.49 Label the sites of torsional and steric strain in each conformation.
a. b. c.
Problem 4.52P Problem 4.53P: 4.51 The eclipsed conformation of is less stable than the
staggered conformation. How much is... Problem 4.54P: (a) Draw the anti and gauche conformations for ethylene glycol . (b) Ethylene glycol
is... Problem 4.55P: For each compound drawn below: a.Label each OH,Br and CH3 group as axial or equatorial. b.Classify... Problem 4.56P: Draw the two possible chair conformations for cis1,3dimethylcyclohexane. Which conformation, if... Problem 4.57P: For each compound drawn below: a. Draw representations for the cis and trans isomers using a hexagon... Problem 4.58P: 4.56 Convert each of the following structures into its more stable chair form. One structure... Problem 4.59P Problem 4.60P Problem 4.61P: Classify each pair of compounds as constitutional isomers, stereoisomers, identical molecules, or... Problem 4.62P Problem 4.63P Problem 4.64P: 4.62 Draw the three constitutional isomers having molecular formula that contain a five-membered... Problem 4.65P Problem 4.66P Problem 4.67P: 4.65 Hydrocarbons like benzene are metabolized in the body to arene oxides, which rearrange to form... Problem 4.68P: Which of the following compounds are lipids? Problem 4.69P Problem 4.70P Problem 4.71P: Cyclopropane and cyclobutane have similar strain energy despite the f act that the CCC bond angles... Problem 4.72P Problem 4.73P: Haloethanes (CH3CH2X,X=Cl,Br,I) have similar barriers to rotation (13.4-15.5kJ/mol) despite the fact... Problem 4.74P Problem 4.75P Problem 4.76P: Consider the tricyclic structure B (a) Label each substituent on the rings as axial or equatorial.... Problem 4.77P: Read Appendix B on naming branched alkyl substituents, and draw all possible alkyl groups having the... Problem 4.78P: Read Appendix B on naming bicyclic compounds. Then give IUPAC name for each of the following... format_list_bulleted