Organic Chemistry 9th Edition solutions

Organic Chemistry 9
Draw complete Lewis structures for the following condensed structural formulas. (a) CH3(CH2)3CH(CH3)2 (b) (CH3)2CHCH2Cl (c) CH3CH2COCN (d) CH2CHCHO (e) (CH3)3CCOCHCH2 (f) CH3COCOOH (g) (CH3CH2)2CO (h) (CH3)3COH

Organic Chemistry 9
Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible. (a) PhCOOCH2CH(CH3)2 (b) PhOCHO (c) PhCH(CH3)COOCH3 (d) PhNHCOCH2CH(CH3)2 (e) CH3CONHCH2Ph (f) CH3CH(OH)CH2CN (g) (CH3)2CHCH2COBr (h) Cl2CHCOCl (i) (CH3)2CHCOOCHO O O C (j) O O (k) PhCONH (l) O

Organic Chemistry 9
Classify the following hydrocarbons, and draw a Lewis structure for each one. A compound may fit into more than one of the following classifications: alkane cycloalkane aromatic hydrocarbon alkene cycloalkene alkyne

Organic Chemistry 9
Write equations for the following acidbase reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, but if you need a hint, you can consult Appendix 4. (a

Organic Chemistry 9
Predict the products of the following SN2 reactions. (a) CH3CH2ONa + CH3CH2Cl (b) CH2CH2Br + NaCN (b) (c) S Na CH3CH2Br + + (c) (d) CH3(CH2)8CH2Cl + Na+ -:CCH (e) N CH3 + I (e) (f) (CH3)3CCH2CH2Br + excess NH3 (g) OH Cl + NaOH (g) (h) Br CH3 NaOH CH3OH

Organic Chemistry 9
Draw Lewis structures for the following compounds and ions, showing appropriate formal charges. (a) [CH3OH2 ]+ (b) NH4Cl (c) (CH3)4NCl (d) NaOCH3 (e) +CH3 (f) -CH3 (g) NaBH4 (h) NaBH3CN (i) (CH3)2OBF3 (j) [HONH3] + (k) KOC(CH3)3 (l) [H2COH]+

Organic Chemistry 9
(a) Draw and name all five isomers of formula C3H5F. (b) Draw all 12 acyclic (no rings) isomers of formula C4H7Br. Include stereoisomers. (c) Cholesterol, C27H46O, has only one pi bond. With no additional information, what else can you say about its structure?

Organic Chemistry 9
Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions. ethanol CH3CH2OH methylamine CH3NH2 acetic acid CH3 C OH O (a) Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. In each case, show the equation for the re

Organic Chemistry 9
Draw the hydrogen bonding that takes place between (a) two molecules of ethanol. (b) two molecules of propylamine. (c) a molecule of dimethyl ether and two molecules of water. (d) two molecules of trimethylamine and a molecule of water.

Organic Chemistry 9
Predict the major products of the following reactions, and propose mechanisms to support your predictions. 1-methylcyclopentene + HBr + CH3 C O O C CH3 O O (a) (phenyl = Ph = ) (b) 1-phenylpropene + HBr + di-tert-butyl peroxide

Organic Chemistry 9
Write a mechanism for the light-initiated reaction of cyclohexane with chlorine to give chlorocyclohexane. Label the initiation and propagation steps.

Organic Chemistry 9
Give IUPAC names for the following compounds. (a) CH3OCH(CH3)CH2OH (b) PhOCH2C

Organic Chemistry 9
Draw a Lewis structure, and classify each of the following compounds: (a) CH3CH2CONHCH3 (b) (CH3CH2)2NH (c) (CH3)2CHCOOCH3 (d) CH3CHCHCOCl (e) (CH3CH2)2O (f) CH3CH2CH2CN (g) (CH3)3CCH2CH2COOH (h) O O (i) O O (j) N CH3 O N CH3 (k) (l) N C O CH3 O O (m) (n) C CH3 O N H COCH3

Organic Chemistry 9
Give the IUPAC names of the following alkanes. (a) CH3C(CH3)2CH(CH2CH3)CH2CH2CH(CH3)2 (b) CH3CH2 CH CHCH3 CH2CH2 CH3 CH CHCH3 CH3 CH3 (c) (d) CH2CH3 CH2CH3 CH3 (e) CH2CH2CH3 CH2CH3 (f) (g) C(CH2CH3)3 (h) CH2CH3 CH(CH3)2

Organic Chemistry 9
Predict the major products of the following substitutions. (a) CH3CH2Br + (CH3)3CO- K+ ethyl bromide potassium tert@butoxide (b) HCC:- Na+ + CH3CH2CH2CH2Cl sodium acetylide 1@chlorobutane

Organic Chemistry 9
Give the structures of the substitution products expected when 1-bromohexane reacts with (a) NaOCH2CH3 (b) KCN (c) NaOH

Organic Chemistry 9
Propose an SN1 mechanism for the solvolysis of 3-bromo-2,3-dimethylpentane in ethanol.

Organic Chemistry 9
The preceding equation for the protonation of acetamide shows a hypothetical product that is not actually formed. When acetamide is protonated by a strong enough acid, it does not protonate on nitrogen, but at a different basic site. Draw the structure of the actual conjugate acid of acetamide, and e

Organic Chemistry 9
Predict which compound in each pair has the higher boiling point. Explain your prediction. (a) CH3CH2OCH3 or CH3CH(OH)CH3 (b) CH3CH2CH2CH3 or CH3CH2CH2CH2CH3 (c) CH3CH2CH2CH2CH3 or (CH3)2CHCH2CH3 (d) CH3CH2CH2CH2CH3 or CH3CH2CH2CH2CH2Cl (e) (e) or NH CH3 N (f) (f) or O NH CH3 NH

Organic Chemistry 9
Give a systematic (IUPAC) name for each alcohol. Classify each as primary, secondary, or tertiary. (a) (a) OH (b) (b) OH Br CHCH3 (c) (c) Cl OH (d) (d) O Br H (e) (e) OH Cl f) (f) OH (g) (g) CH2OH