Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 3, Problem 3.49P
Label the electrophilic and nucleophilic sites in each molecule.
a.
c.
e.
b.
d.
f. 
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a.
5. Draw the product(s) of each addition reaction
b.
d.
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HBr
H2SO4, H₂O
Bra, H2O
a. 9-BBN
b. H2O2, NaOH
76%
4. Classify each structure below as a nucleophile or electrophile (or both) and briefly explain your choice.
a. N31- (the azide ion)
C.
phenol
b. H3O+ (the hydronium ion)
Which is a better nucleophile? a. Br− or Cl− in H2O b. Br− or Cl− in DMSO c. CH3O− or CH3OH in H2O d. CH3O− or CH3OH in DMSO e. HO− or −NH2 in H2O f. HO− or −NH2 in DMSO g. I− or Br− in H2O h. I− or Br− in DMSO
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 3.1PCh. 3 - Prob. 3.2PCh. 3 - Draw the structure of a compound fitting each...Ch. 3 - Draw structures that fit each description and name...Ch. 3 - What types of intermolecular forces are present in...Ch. 3 - Prob. 3.6PCh. 3 - Explain why the boiling point of propanamide, is...Ch. 3 - Predict which compound in each pair has the higher...Ch. 3 - Prob. 3.9PCh. 3 - Prob. 3.10P
Ch. 3 - a Label the hydrophobic and hydrophilic portions...Ch. 3 - Prob. 3.12PCh. 3 - Prob. 3.13PCh. 3 - Prob. 3.14PCh. 3 - Prob. 3.15PCh. 3 - Nonactin and valinomycin each contain only two...Ch. 3 - Prob. 3.17PCh. 3 - Problem 3.26 Label the electrophilic and...Ch. 3 - Problem 3.27 Considering only electron density,...Ch. 3 - The fact that sweet-tasting carbohydrates like...Ch. 3 - 3.29
Identify the functional groups in the...Ch. 3 - Prob. 3.22PCh. 3 - 3.32 Identify the functional groups in each...Ch. 3 - Draw the seven constitutional isomers having...Ch. 3 - 3.33 Identify each functional group located in the...Ch. 3 - Draw seven constitutional isomers with molecular...Ch. 3 - Prob. 3.27PCh. 3 - Prob. 3.28PCh. 3 - Prob. 3.29PCh. 3 - Intramolecular force of attraction are often...Ch. 3 - 3.40 (a) Draw four compounds with molecular...Ch. 3 - Prob. 3.32PCh. 3 - Explain why CH3CH2NHCH3 has higher boiling point...Ch. 3 - Prob. 3.34PCh. 3 - Prob. 3.35PCh. 3 - Explain the observed trend in the melting points...Ch. 3 - Prob. 3.37PCh. 3 - Prob. 3.38PCh. 3 - Prob. 3.39PCh. 3 - 3.48 Explain why diethylether and have similar...Ch. 3 - Prob. 3.41PCh. 3 - 3.50 Predict the solubility of each of the...Ch. 3 - Prob. 3.43PCh. 3 - Prob. 3.44PCh. 3 - THC is the active component in marijuana, and...Ch. 3 - Prob. 3.46PCh. 3 - Prob. 3.47PCh. 3 - Prob. 3.48PCh. 3 - Label the electrophilic and nucleophilic sites in...Ch. 3 - By using only electron density arguments,...Ch. 3 - Prob. 3.51PCh. 3 - Prob. 3.52PCh. 3 - Prob. 3.53PCh. 3 - Prob. 3.54PCh. 3 - Prob. 3.55PCh. 3 - Recall from section 1.10B that there is restricted...
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- Rank the species in each group in order of increasing nucleophilicity. a. CH,, "OH, "NH2 b. H20, OH, "SH in CH3OH c. CH,CH2S", CH;CH2O¯, CH;COO" in CH3OH d. CH3NH2, CH3SH, CH;OH in acetone e. "OH, F", CI" in acetone f. HS, F", CI in CH3OHarrow_forwardDraw the organic product(s) formed when CH3CH2CH2OH is treated with each reagent. a.H2SO4 b.NaH c.HCl + ZnCl2 d.HBr e.SOCl2, pyridine f.PBr3 g.TsCl, pyridine h. [1] NaH; [2] CH3CH2Br [1] i.TsCl, pyridine; [2] NaSH j.POCl3, pyridinearrow_forwardWhat is the major product of the following reaction? A. B. NO₂ NO₂ NO₂ CH3CI, AICI3 C. D. NO₂ NO₂arrow_forward
- Which is the major organic product of this reaction? A. B. 4 ОА O OB O C COD AICI3 benzene C. D.arrow_forward1. Which carbonyl group of the given compound is most reactive for nucleophilic addition reaction? a. All have equal reactivity b. Carbonyl Group 1 c. Carbonyl Group 2 d. Carbonyl Group 2. An aldehyde commonly exhibits a nucleophilic addition type of reaction. When a nucleophile attacks a carbonyl carbon, what happens to the oxygen atom in the structure? Refer to the structure below. ~ a. Oxygen atom becomes more electronegative. b. Oxygen atom obtains a net negative charge. c. Oxygen atom transforms to an alkoxide group. d. Oxygen atom acts as the new electrophile. 3. Assign the trivial name of the structure below. a. Diphenylketone b. Benzyl phenylketone c. Diphenyl aldehyde d. Benzyl phenyl aldehydearrow_forwardDoes the equilibrium favor the reactants or products in each substitution reaction? a. CH;CH2-NH2 Br CH;CH2-Br + "NH2 b. "CN CN + I-arrow_forward
- S Determine the product(s) for each reaction. HD TSO H X H CI X H H CI H OTS A. B. C. D. HO HO TSO H "H LOH HD TSCI pyridine SOCI₂ pyridine ΚΙ HCI ZnCl₂arrow_forwardRank the species in each group in order of increasing nucleophilicity. a. CH3CH2S−CH3CH2O−, CH3CO2− in CH3OH b. CH3NH2, CH3SH, CHOH in acetone c.−OH, F−, Cl− in acetone d. HS−, F−, Cl− in CH3OHarrow_forwardwodn 3. Identify the mechanism (SN1 or SN2) for the substitution product of the following reactions. Draw the substitution product. a. b. ***** Br Br SNa MeOH heatarrow_forward
- What is the product of the following reaction? A. B. شما NH NH2Et, cat H* C. ZI avant HO. D. `N OHarrow_forward1. Which of the following organic compounds is the least polar? a. CH3CH2CHO b. CH3COCH3 c. CH3CH2CH2OH d. CH3CH2OCH3 e. CH3COOH 2. Which reagent can be used to convert acetic anhydride to acetic acid? a. NH3 b. CH3COO- c. CH3OH d. None of these e. H2Oarrow_forwardReagents a. C6H5CHO b. NaOH, ethanol h. BrCH2CH=CH2 i. Na* OEt, ethanol j. Br2, H* k. K* t-BuO c. Pyrrolidine, cat. H* d. H2C=CHCN e. H3O* f. I. CH2(CO2ET)2 -CH2CH2CN LDA m. heat g. ELOC(=0)CO2ET Select reagents from the table to synthesize this compound from cyclopentanone. Enter the letters of the chosen reagents, in the order that you wish to use them, without spaces or punctuation (i.e. geda).arrow_forward
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