Which resonance form best explains the increased acidity of p-nitrophenol compar

Question

Which resonance form best explains the increased acidity of p-nitrophenol compared to phenol? 17. 12. What is the major product from the reaction of 2-hexamol with H CrO? c) CI b(C112).CF?OH d) Cl tOHhCCHs 13. Which of these reagents would be best to OH (A) D,O, catalytic HCI (B) D,O, in CH,COOH (C) NaOD in CH,CH,OD, then aqueous work Note Questions 18-20 refer to the following sequence dry ether 2) HO (D) NaBD, in CHCH,OH, then aqueous 18. What is compound I? wock-up d) PhCH:P e) PhCH 14. What are the products from the following reaction? 19. What is compound a) PhCH Mg b)PhCH:MgBr c) PhCH e) PhCH OMgBr 20. What is compound I11? a) PhCH OCH OH e) PhCH CHO c) PhCH OCH CH b) PhCH CHBrCHs 21. In order to form a carboxylic acid, you would react a 15. Which step in the following ether cleavage cannot occur? Grignard reagent with a) an aldehyde c) a ketone b) an epoxide d) carbon dioxide e) an ester 22. How could the following synthesis be accomplished? OH (1) SOC?. (2) Mg, ether, (3) CHO, then H30. 16. Arrange the following phenols in order from the most a) b) (1) SOCl2. (2) Li, ether, (3) (CHCH?Culi, acidic to least acidic. (4) KMnoi, OH d) (1) PBr, (2) Mg, ether, (3) à then Hy0 I I IVV a)1>11 > Ill > IV > V b) III>I> IV> V cIII>V > III> IV (4) PCC,CH Ch e) (I) PCh, (2) Mg, ether,(3) CHjCH then PCC

Explanation / Answer

12.

(D)

CH3CH2CH2CH2CHOHCH3 --- H2CrO4------> CH3Ch2CH2CH2COCH3

13.

(D)

14.

(d) Phenol and benzyl iodide

15.

(c)

16.

(b) II > I > III > IV > V

Electron withdrawing group increase the acidity of phenol but electron donating groups decrease the acidity of phenol

17.

(D)

18.

(C)

19.

(b)

20 .

(d)

21.

(d)

22.

(d)

23.

(D) CH3CHOHCH2CHO + CH4

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