235 Organic II. Final Exam Review REACTIONS OF CONJUGATED DIENES 1,2 VS 1,4 ADDITION REACTIONS OF CONJUGATED DIENES

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1 b. the ompound 7 i 1 Spectral Data: singlet, ppm singlet, 14.1 ppm singlet, 14.4 ppm doublet, 19.1 ppm doublet, 18.5 ppm 1 MR Mass Spectrum Absorbance Intensity Infrared Spectrum Structure: 119 m/e Wave umber, cm Wavelength, microns ppm,..... a aisen condensation an aldol condensation alkylation of an enamine hemistrynline, rganic II Final Exam Review hemistry 5 Sample First our Exam All multiple choice and short answer questions are points each; others as marked. hemistry 5, Fall Sample Second our Exam Data for the mass spectrum, the 1 and 1 MR and the IR spectrum for a compound 9 10 are given below. Based on the spectral information provided, suggest a structure for this compound and write the structure clearly in the space provided below. Also, in the spaces provided, clearly indicate the information which you obtained from each spectral source. (5 points for each spectrum, 5 points for the correct structure; 5 points total) data, are given below. Elemental Analysis:, 80.56;, 7 In the space below, write an acceptable IUPA name for the molecule shown on the right: Suggest a synthesis for each of the compounds shown on the right using the method shown under the compound. early show reagents/reactants required next to the numbers on the arrow; you may add additional "numbers" if necessary. (4 points per box ) Section I omenclature & M/ (4 points each) In the space provided, give the correct IUPA name for the compound shown on the right. REATIS F JUGATED DIEES Just like alkenes, conjugated dienes undergo the ionic addition of ; however, the addition to conjugated dienes proceeds by two pathways.. In the space below, write an acceptable IUPA name for the molecule shown on the right:. In the space below, write an acceptable IUPA name for the molecule shown on the right: 4. Which of the following is true regarding the 1 MR of carbonyl compounds: a. in the proton-coupled 1 MR, aldehyde carbons will appear as doublets b. aldehydes and ketones will typically absorb at values 00 ppm c. the carbonyl absorbance from a ketone will always appear as a singlet d. answers a) and c), only, are correct. e. answers a), b) and c) are all correct. 5. hlorine exists as two major isotopes; 5, 75%, and 7, 5%. In the mass spectrum, a compound with one chlorine atom will have: a. two molecular ions, in the ratio :1 b. four molecular ions, in the ratio 1:::1 c. two molecular ions, in the ratio :1 d. two molecular ions, in the ratio 1: 1 e. three molecular ions, in the ratio 1::1 6. The base peak in the mass spectrum of toluene,, is most likely to be due to: a. b. c. d. e. 7. The major bands in the infrared spectrum of benzyl alcohol will be: a. 150 cm -1 ; 00 cm -1 ; 1610 cm -1 ; 1450 cm -1 b. 450 cm -1 ; 100 cm -1 ; 90 cm -1 ; 1760 cm -1 c. 90 cm -1 ; 450 cm -1 ; 1610 cm -1 d. 450 cm -1 ; 100 cm -1 ; 90 cm -1 ; 1600 cm -1 e. 450 cm -1 ; 100 cm -1 ; 00 cm -1 ; 1600 cm Which of the following is not true regarding the spectra of 4-methylbenzonitrile: 1 a. in the 1 MR, the phenyl group will appear as two doublets MR will have two singlets and two doublets in the aromatic region c. the IR spectrum will display by a significant absorption at about 00 cm -1 d. in the 1 MR, the group will absorb at approximately. ppm e. in the mass spectrum, the base peak will most likely be at m/z = 91 quartet,.8 ppm quartet, 0.9 ppm Which of the compounds shown below would be most consistent with the following 1 spectral data: quartet,.0 ppm; quartet, 50.0 ppm; doublet, 19.1 ppm ; singlet, 17.5 ppm; doublet, 19.7 ppm; singlet, 14.8 ppm; singlet, ppm a. b. c. d. e. 5. In the tetrahedral intermediate formed in an acyl transfer reaction, the best anionic leaving group will be: a. the strongest base b. the most stable anion c. the group with the highest pk a d. the phenoxy group e. the group having the weakest conjugate acid Which of the following is correct regarding the spectroscopy of acyl compounds? a. the frequency of the carbonyl absorbance of acyl compounds in the IR generally parallels reactivity of the acyl carbonyl towards nucleophilic addition b. in the mass spectrum, the most common fragmentation of acyl compounds is expulsion of carbon monoxide c. the 1 MR absorbance of carboxylic acid protons is very highly deshielded d. a and c, only, are correct statements e. a, b and c are correct statements an acetoacetic ester synthesis an intramolecular aldol condensation Reproduction or distribution of any of the content, or any of the images in this presentation is strictly prohibited without the expressed written consent of the copyright holder , addition 1,4 addition hemistrynline, REATIS F JUGATED DIEES In the 1,4-addition, protonation on the terminal carbon generates the allylic carbocation, with cationic character on both carbons #1 and #. REATIS F JUGATED DIEES In the 1,4-addition, protonation on the terminal carbon generates the allylic carbocation, with cationic character on both carbons #1 and #. - allylic carbocation hemistrynline, The addition of to carbon #1 of the diene gives the 1,4-addition product. hemistrynline, , VS 1,4 ADDITI REATIS F JUGATED DIEES For 1, and 1,4-additions the following trends are observed: REATIS F JUGATED DIEES The two products are also referred to as the kinetic product; and the thermodynamic product. The 1,-addition product forms rapidly at low temperatures. The 1,4-addition product is predominant at higher temperatures. Even at low temperatures, 1,4-addition products will predominate if given enough time. The addition of to butadiene is reversible and isolated 1,-addition product will convert to the 1,4-product at higher temperatures or at longer times. 1 Kinetic product (faster). 4 Thermodynamic product (slower, but more stable). 1, addition 1,4 addition hemistrynline, hemistrynline,

2 hemistrynline, I-LASS PRBLEM Predict the major products for the following reactions: 1,-addition 1,4-addition REATIS F JUGATED DIEES The Diels-Alder reaction; 4 ycloadditions. a diene......and a dienophile heat 1,-addition 1,4-addition This is called an electrocyclic reaction. hemistrynline, REATIS F JUGATED DIEES The Diels-Alder reaction; 4 ycloadditions. heat heat heat TE (4 ) RULE The resonance description of benzene will explain the geometry of the molecule and the isomer distribution of benzene derivatives, but does not explain the unusual stability of benzene and its derivatives. The stability of benzene is suggested to arise from the fact that the conjugated π system is planar and contains 4n electrons (with n = 1), and it is suggested that all compounds having planar, conjugated π systems containing 4n electrons will share this stability. This property, described originally by ückel, is referred to as aromaticity. hemistrynline, hemistrynline, TE (4 ) RULE onsider the following molecules: TE (4 ) RULE onsider the following molecules: 4 π electrons not aromatic 6 π electrons aromatic 8 π electrons not aromatic 6 π electrons aromatic 6 π electrons aromatic hemistrynline, hemistrynline,

3 hemistrynline, REATIS F ARMATI SIDE-AIS xidation with neutral Mn Mn 4 /, heat REATIS F ARMATI SIDE-AIS Mn 4 - /, heat Mn 4 - /, heat Mn 4 - /, heat Mn 4 - /, heat hemistrynline, REATIS F ARMATI SIDE-AIS Allylic bromination with BS REATIS F ARMATI SIDE-AIS Dissolving Metal Reduction of Benzene Derivatives The Birch Reduction BS/ 4 "radical initiator" Li/ BS/ 4 "radical initiator" Li/ BS/ 4 "radical initiator" Li/ hemistrynline, hemistrynline, REATIS F ARMATI SIDE-AIS ELETRPILI ARMATI SUBSTITUTI Predict the products of the following reactions Predict the products of the following reactions. X R BS/ 4 "radical initiator" X alogenation R Acylation Mn 4 - / itration Sulfonation Alkylation R S R Li/ S hemistrynline, hemistrynline,

4 hemistrynline, ALGEATI REATIS ITRATI REATIS Fe S 4 /Fe /Al S 4 /Fe /Al hemistrynline, SULFATI REATIS FRIEDEL-RAFTS ALKYLATI S 4 S S S 4 - Fe S S S S 4 Fe hemistrynline, hemistrynline, FRIEDEL-RAFTS ALKYLATI FRIEDEL-RAFTS AYLATI Fe Fe Reaction limited to alkyl halides; aryl or vinyl halides do not react.. Reaction does not occur on rings containing strong electron withdrawing substituents. S Fe R R. Multiple substitutions often occur. 4. arbocation rearrangements can occur, particularly with 1 alkyl halides. R hemistrynline, hemistrynline,

5 hemistrynline, FRIEDEL-RAFTS AYLATI I-LASS PRBLEM Fe Fe Multiple substitutions do not occur.. arbocation rearrangements do not occur.. Reaction does not occur on rings containing strong electron withdrawing substituents. 4. Acid anhydrides can also be used. S / S 4 Al hemistrynline, REATIVITY F SUBSTITUTED BEZEES I-LASS PRBLEM: Strongly Activating Strongly Deactivating F S I R R R ortho & para directing meta directing S /Fe /Fe I /u hemistrynline, hemistrynline, I-LASS PRBLEM I-LASS PRBLEM S /Fe ortho isomer S /Fe Reactions that yield alcohols: - B 4. ( ) ( ) hemistrynline, B 4. - B 4. hemistrynline,

6 hemistrynline, I-LASS PRBLEM Reactions that yield alcohols: LiAl 4, ether. I-LASS PRBLEM Reactions that yield alcohols: Mg/ether. LiAl 4, ether. Mg/ether. LiAl 4, ether. Mg/ether. hemistrynline, I-LASS PRBLEM Reactions that yield alcohols: LiAl 4, ether. from a carboxylic acid I-LASS PRBLEM Suggest two syntheses for the molecule shown below, using a Grignard Reaction. LiAl 4, ether. from an ester Mg, ether. from an ester hemistrynline, hemistrynline, I-LASS PRBLEM Utilizing any one of the starting materials shown on the right, suggest a synthesis of the following compound: I-LASS PRBLEM Utilizing any one of the starting materials shown on the right, suggest a synthesis of the following compound: hemistrynline, hemistrynline,

7 hemistrynline, I-LASS PRBLEM Predict the products for the following substitution reactions. -- I-LASS PRBLEM Predict the products for the following reactions of epoxides.. / Mg, ether / Tos -. / hemistrynline, I-LASS PRBLEM Beginning with benzyl bromide, suggest a synthesis of the compound shown below: I-LASS PRBLEM Beginning with benzyl bromide, suggest a synthesis of the compound shown below: hemistrynline, hemistrynline, ARBYL DESATI REATIS The base-catalyzed condensation of two aldehydes or ketones to form a β-hydroxy aldehyde or ketone is known as the Aldol ondensation. - - hemistrynline, ARBYL DESATI REATIS The base-catalyzed condensation of two moles of an ester is called the aisen ondensation. - - hemistrynline,

8 hemistrynline, ARBYL DESATI REATIS An intramolecular aisen is called the Dieckman ondensation. - - REATIS F α,β-usaturated ARBYLS The Michael Reaction of α,β-unsaturated ketones and aldehydes. β onjugated ketones and aldehydes can undergo an analogous reaction in which a nucleophile adds to the terminal carbon of the double bond. uc α uc uc hemistrynline, REATIS F α,β-usaturated ARBYLS The Michael additions of α,β-unsaturated ketones and aldehydes that we covered include: ( ( ) ) Al Al ( ( ) ) uli uli hemistrynline, REATIS F α,β-usaturated ARBYLS Enolate anions also undergo the Michael Reaction: hemistrynline, REATIS F α,β-usaturated ARBYLS Michael addition of enamines and nitroalkanes. I-LASS PRBLEM -Buten--one is subjected to the four steps shown below; what will be the major product of this reaction sequence? -. / ; heat. - / 4. /. / hemistrynline, hemistrynline,

9 hemistrynline, I-LASS PRBLEM Beginning with cyclohexanone, suggest a simple synthesis for the following compound: I-LASS PRBLEM Beginning with cyclohexanone, suggest a simple synthesis for the following compound: -. / hemistrynline, I-LASS PRBLEM Beginning with cyclohexanone, suggest a simple synthesis for the following compound: I-LASS PRBLEM Beginning with cyclohexanone, suggest a simple synthesis for the following compound: hemistrynline, hemistrynline, I-LASS PRBLEM Predict the products for the following reactions: I-LASS PRBLEM Predict the products for the following reactions: - K S. - / ab. a. heat, hemistrynline, hemistrynline,

10 hemistrynline, I-LASS PRBLEM Predict the products for the following reactions: FRMATI F DIAZIUM SALTS a,, S 4 (excess). Ag,, heat...a diazonium salt... hemistrynline, REATIS F DIAZIUM SALTS P, REATIS F DIAZIUM SALTS K, u, u /, u KI hemistrynline, hemistrynline, ITEGRATED SPETRSPY: MPUD #1 ITEGRATED SPETRSPY: MPUD # MW = MW = Wave umber, cm Intensity Absorbance m/e Wavelength, microns 400 cm -1 : 100 cm -1 : 900 cm -1 : 750 cm -1 : 1710 cm -1 : 1610 cm -1 : hemistrynline, hemistrynline,

11 hemistrynline, ITEGRATED SPETRSPY: MPUD #1 ITEGRATED SPETRSPY: MPUD # 9 10 MW = MW = Intensity m/e 1 Spectral Data: singlet, ppm singlet, 14.1 ppm singlet, 14.4 ppm doublet, 19.1 ppm doublet, 18.5 ppm quartet,.8 ppm quartet, 0.9 ppm ppm, 0 hemistrynline, ITEGRATED SPETRSPY: MPUD # Wave umber, cm MW = ITEGRATED SPETRSPY: MPUD # 5 9 MW = 180 Absorbance Wavelength, microns 400 cm -1 : 100 cm -1 : 900 cm -1 : 00 cm -1 : 1710 cm -1 : 1610 cm -1 : 1 Spectral Data: singlet, 17.0 ppm; triplet, 59.5 ppm; doublet, 57.7 ppm; quartet, 0.4 ppm; quartet, 6 ppm ppm, 0 hemistrynline, hemistrynline,

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