ps2 - F G CH 3 CH 2 CH 3 O H O CH 2 OCH 3 H B F (5) Using...

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
Chemistry 3590 Honors Organic Chemistry I PROBLEM SET #2 FALL, 2009 Please answer problems 48, 51, 57 and 58 in Chapter 2 of Bruice. Also answer the following questions: (1) Draw the preferred conformation of trans -3-methylcyclohexanol in realistic perspective. (2) Using realistic perspective, draw the most stable conformations of structures A and B shown below. Be sure to indicate all hydrogen atoms on the ring. CH 3 CH 3 CH 3 CH 3 O A B (3) Circle the nucleophilic atom or group in each of the following molecules C-E. If a molecule has more than one nucleophile, circle the best one. C D E O H 2 N CH 2 OCH 3 CH 3 CH 3 O (4) Circle the electrophilic atom or group in each of the following molecules F-H. If a molecule has more than one electrophile, circle the best one.
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: F G CH 3 CH 2 CH 3 O H O CH 2 OCH 3 H B F (5) Using the "curved arrow" formalism, indicate how the following three pairs of nucleophiles and electrophiles would react: E + H , D + F , C + G [Note: If a molecule has more than one nucleophilic or electrophilic site, use the most reactive one. And just show the first product, even though it may undergo further reactions] (6) This one will require some careful thought and analysis. The G o for the conformational equilibrium shown below is 8.4 kJ/mol (i.e. conformer I is favored). Use this information to estimate the energy cost of a 1,3-diaxial interaction between two methyl groups on a 6-membered ring. CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 H 3 C I J...
View Full Document

This note was uploaded on 11/10/2009 for the course CHEM 1570-001 taught by Professor Tadhgbegley during the Fall '08 term at Cornell University (Engineering School).

Ask a homework question - tutors are online