Problem 6-24 The addition of water to ethylene to yield ethanol has the following thermodynamic parameters: AH° = -44 kJ/mol H2C=CH2 + H2O CH3CH2OH AS-0.12 kJ/(K⚫ mol) Keq = 24 (a) Is the reaction exothermic or endothermic? (b) Is the reaction favorable (spontaneous) or unfavorable (nonspontaneous) at room temperature (298 K)? Problem 6-27 Draw the complete mechanism for each of the following polar reactions. HCL (a) (b) HBr (c) HCL Cl Br Problem 6-29 Identify the functional groups in the following molecules, and show the polarity of each: (a) CH3CH2C=N CH, CH, COCH (c) CH3CCH2COCH3 NH2 (e) OCH3 (b) (d) O Problem 6-30 Identify the following reactions as additions, eliminations, substitutions, or rearrangements: (a) CH3CH2Br + NaCN CH3CH2CN ( + NaBr) Acid -OH (+ H2O) catalyst (b) + (c) Heat NO2 Light + 02N-NO2 (+ HNO2) (d)

What are the missing reagent(s) for the reaction below? (Select all that apply? OH PBr3 A ☐ A C B D 1) ??? 2) NaCN SOCI₂ NEt3 B TSCI NEt3 с с CN HCN D

PROBLEM 3-4 Provide IUPAC names for the following compounds. (a) (CH3)2CHCH½CH3 (b) CH3— С (СН3)2 — СHз - CH,CH, CH, CH,CH, (c) CH,CH,CH,CH–CH(CH,), (d) CH,-CH-CH,-CH-CH, | Ç(CH,), CH,-CHCH,CH, e) CH,CH,CHCHCH, (f) (CH,),C-CH–CH,CH,CH, CH(CH,),

PROBLEM 3-3 Write structures for the following compounds. (a) 3-ethyl-4-methylhexane (b) (d) (c) 4-tert-butyl-2-methylheptane 3-ethyl-5-isobutyl-3-methylnonane 5-isopropyl-3,3,4-trimethyloctane

PROBLEM 3-16 Which of the following cycloalkanes are capable of geometric (cis-trans) isomerism? Draw the cis and trans isomers. (a) 3-ethyl-1,1-dimethylcyclohexane (c) 1-ethyl-3-methylcyclopentane (b) 1-ethyl-3-methylcycloheptane (d) 1-cyclopropyl-2-methylcyclohexane

PROBLEM 3-31 Name the following compounds. (b) O (d)

PROBLEM 1-9 Draw the important resonance forms of the following cations and anions: (a) (b) (c) (e) + CH3O–CH–CH=CH–NH NH₂ + OH H₂C=CH-C=OH H3C-C-CH-CH=CH-CN (d) H H₂N-CH=CH-C-OCH3 H3C-CH-C-CH=CH-CN NH || H₂C=CH-C-CH₂

PROBLEM 3-2 Name the following alkanes and haloalkanes. When two or more substituents are present, list them in alphabetical order. (a) CH₂ CH3 CH₂-CH-CH₂-CH₂ (Sd-592) Ivjud-riboser adi lo comes T soitujzdus ivalla to sergab snt no boand sas aquorg rivud-1 Br CH₂CH3 POTCH3-CH-CH-CH3 nothing (b) (2) cimbrogaz (c) CH–CH, CH,CH(CH,), 1 Todll trong (cruiol sda ba H I TOLE asilo sao CH₂-CH₂-CH-CH-CH₂-CH₂-CH₂ (d) CH₂-CH-CH₂ CH₂ CH₂ T CH-CH₂-CH₂-CH₂-CH₂-CH₂-CH-CH-CH₂

PROBLEM 4-25 In the presence of a small amount of bromine, cyclohexene undergoes the following light- promoted reaction: + trace Br₂ hv cyclohexene (a) Propose a mechanism for this reaction. (b) Draw the structure of the rate-limiting transition state. Br 3-bromocyclohexene + HBr

PROBLEM 11-38 Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents. (a) trans-cyclopentane-1,2-diol (b) 1-chloro-1-ethyleyclopentane f (c) OCH, CH₂ (e) OCH₂CH₂ C-CH₂CH₂ (1) OCH,