Problem_Set_3 - antiaromatic character H H...

Info iconThis preview shows pages 1–2. Sign up to view the full content.

View Full Document Right Arrow Icon
Chem 358 Spring 2007 Problem Set #3 Chapter 16 : 16 .11, 15, 19, 23, 24, 29, 38(a) and (c), 40, 44, 47, 48, 49, 54, 55, 57 Additional problems 1. Propose a mechanism using the curved arrow formalism for the reaction shown below. H + 2. [From 2006 Prelim I) Cations A-D initially form during electrophilic aromatic substitutions with Br 2 /FeBr 3 . After considering other important resonance structures rank the cations in order of increasing stability. Br Br CH 3 O Br O 2 N Br NO 2 A B C D 3. [From 2006 Prelim I] Propose a synthesis of the following compounds from benzene by filling in the reagents needed as well as the isolable intermediate product along the way. You can disregard the possible formation of minor isomers. SO 3 H NO 2 4. The compound shown below, called 1,6-methano[10]annulene, exhibits two sets of signals in the 1 H NMR spectrum at δ = 7.10 (8 H) and -0.50 (2 H) ppm. Is this a result of aromatic character or
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 2
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: antiaromatic character? H H 1,6-methanoannulene[10] 5. The 1 H NMR spectrum of the most stable isomer of [14]annulene shows two signals at δ = -0.61 (4 H) and 7.88 (10 H) ppm. Two possible structures (A and B) for [14]annulene are shown below. Which one corresponds to the NMR spectrum described? Give reasons for your answers. A B 6. Rank the following in order of decreasing reactivity in electrophilic aromatic substitution. CF 3 CH 3 CH 3 CF 3 CH 3 CH 3 A B C D 7. Propose a reasonable synthesis for the following compounds from benzene. O NO 2 Cl (a) (b) 8. (From 1999 Final Exam) Complete the following reactions by drawing the major product that would be formed. NO 2 NO 2 NO 2 NO 2 NO 2 Br NH 2 NO 2 Cl 2 AlCl 3 Br 2 FeBr 3 HNO 3 H 2 SO 4 Cl 2 AlCl 3...
View Full Document

This note was uploaded on 04/22/2009 for the course CHEM 3570 taught by Professor Ganem, b during the Fall '06 term at Cornell.

Page1 / 2

Problem_Set_3 - antiaromatic character H H...

This preview shows document pages 1 - 2. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online