1.What would be the proper name of the following compound? HC HC-C-C三C-H OH 1.1-dimethyl-2-propyn-1-ol 日2022 2.What would be the product of the following reaction sequence? 1.NaNH2 H,C-C三CH 2.CHCHO 3.D,0 A) D0-C-CH2-C三CH B)HC-C三CD C) HC-C三C-CH2-CH2-OD D) OD HC-C三C C-CH3 E) H H0-CCH,-C三CD CH3 Ans:D Page
Page 1 1. What would be the proper name of the following compound? H3CCC H3C C H OH A) 1,1-dimethyl-2-propyn-1-ol D) 2-methyl-3-butyn-2-ol B) 3-methyl-1-butyn-3-ol E) 2-ethynyl-2-propanol C) 3-hydroxy-3-methyl-1-propyne Ans: D 2. What would be the product of the following reaction sequence? H3C C CH ? 1. NaNH2 2. CH3CHO 3. D2O A) C CH2 C CH H DO CH3 B) H3C C CD C) H3C C C CH2 CH2 OD D) H3C C C C CH3 OD H E) C CH2 C CD H HO CH3 Ans: D
3.What would be the product of the following reaction? CH2-CEC-H H20 cat.H2SOa cat.HgSO, CH2-C三C-OH c) OH Ans: Page2
Page 2 3. What would be the product of the following reaction? CH2 CCH ? H2O cat. H2SO4 cat. HgSO4 A) CH2 CH2 C O H B) CH2 C C OH C) CH2 CH CH2 OH OH D) CH2 C CH2 OH E) O CH2 C CH3 Ans: E
4.What would be the product of the following reaction? CH2-CEC-CH3 1 atm H Lina CH2CH2.CH2-CH cl-cac-i D) CHz-CH2-CH2-CH Ans:I Page3
Page 3 4. What would be the product of the following reaction? A) CH2 CH2 CH2 CH3 B) CH2 C C H CH3 H C) CH2 CCH D) CH2 C C CH3 H H E) CH2 CH2 CH2 CH3 Ans: D
5.What would be the product of the following reaction sequence? 1.Br2 2.excess NaNH2 Br -CH Br Ph (racemic) P从Br (meso) C)Ph-C=C-Ph D) Br Ph-CHECph E) Ph、 NH2 CH-CH NH Ph Ans: 6.Given separate pure samples,in what way(s)could you quickly distinguish between the two alkynes below -czc-n and -C=C-D C)ultraviolet spectroscopy Ans:E
Page 4 5. What would be the product of the following reaction sequence? CH CH 1. Br2 2. excess NaNH2 ? A) C C Br Br Ph H Ph H (racemic) B) C C Br Br Ph H Ph H (meso) C) Ph C C Ph D) CH C Br Ph Ph E) CH CH NH2 NH2 Ph Ph Ans: C 6. Given separate pure samples, in what way(s) could you quickly distinguish between the two alkynes below? CCH and CCD A) gas chromatography D) NMR spectroscopy B) infrared spectroscopy E) both B and D C) ultraviolet spectroscopy Ans: E
7.What would be the major product expected from the following reaction?(Notice the D sotope.) 1. B-D H-C=C-CH-CH; 7 2.H2O2,NaOH H CH-CH3 HO B) CH: CH-CH3 OH c) CH CD-CH; H:C- CH -CHD-CH-CH E) CH; CH-CH3 DH2C- Ans:D Page5
Page 5 7. What would be the major product expected from the following reaction? (Notice the D isotope.) H C C CH CH3 CH3 B D ? 2. H2O2, NaOH 1. A) H C C CH CH3 CH3 HO D B) H C C CH CH3 CH3 D OH C) H3C C CD CH3 CH3 O D) O C CHD CH CH3 CH3 H E) DH2C C CH CH3 CH3 O Ans: D
8.What would you expect the major product of the following reaction sequence to be? ○-cE-H H20 HgSO B) ○-cEc-oH 9 D8c D-ch:-Eu Ans:D Page6
Page 6 8. What would you expect the major product of the following reaction sequence to be? ? H2O H2SO4 HgSO4 CCH A) C O CH2 CH3 B) C C OH C) C H C H OH D) C O CH3 E) CH2 C H O Ans: D
9.What is the major product expected from the following reaction? 1)NaNH2 NH3 (liquid) 3/ Page7
Page 7 9. What is the major product expected from the following reaction? C C H 1) NaNH2 / NH3 (liquid) 2) iodoethane 3) Lindlar's catalyst / H2 ? A) B) C) D) E) Ans: D
10hhoheeo Na/NH3(iq） ·® H:C-C=C-CHs } c) c--8-c Ans:A Page8
Page 8 10. Considering the mechanism of the following reaction, which of the intermediates shown below is not likely to form along the reaction pathway? Na / NH3 (liq) A) H3C C C CH3 B) H C) H D) H E) H3C C C CH3 Ans: A
11.What major product(s)are expected from the reaction shown below? H,C一C三C-CH HBr(exces9）→？ H Br H:C CH; B) Br H:C CH; C) H Br H一C 一B Br H H-C Br E)more than one of the above Ans:C 12.What organic product results from the reaction shown below? CaC2+H2O CH:CH D Ca(OH)z HC=CH E HOH Ans:D Page9
Page 9 11. What major product(s) are expected from the reaction shown below? H3C C C CH3 HBr (excess) ? A) H3C C C CH3 H Br B) H3C C C CH3 Br Br C) H3C C C CH3 H Br H Br D) H3C C C CH3 H Br Br H E) more than one of the above Ans: C 12. What organic product results from the reaction shown below? CaC2 + H2O ? A) CH4 B) Ca(CH3)2 C) CH3CH3 + Ca(OH)2 D) HC CH E) H C H OH OH Ans: D
13.What is the major product of the following reaction? 1)NaNH2 Ans:C 14.Which,if either,of the following hydrogenations would be the more exothermic? H,C-CEC-CH,4、 H,C、 C=c CH3 H2 CH:CH2CH2CH: Pt H H Pt Step 1 Step 2 A)Step1 D)neither is exothermic Step 2 E)there is no way to predict this both are equally exothermic A Page 10
Page 10 13. What is the major product of the following reaction? 1) NaNH2 2) Br ? A) B) C) D) NH2 E) Ans: C 14. Which, if either, of the following hydrogenations would be the more exothermic? H3C C C CH3 H2 Pt H3C C C CH3 H H H2 Pt CH3CH2CH2CH3 Step 1 Step 2 A) Step 1 D) neither is exothermic B) Step 2 E) there is no way to predict this C) both are equally exothermic Ans: A