Assign 6-1 - 2 mechanism, the nucleophile bonds to the...

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
Exercise 1 Chapter 6 1. Predict the product(s) of each substitution reaction below. In reactions (a) – (h), indicate the most likely mechanism (S N 1 or S N 2) C CH 3 H 3 C CH 3 Br C CH CH HC CH CH CH 2 I CH 2 CH 2 CH 2 CH 3 Cl CH 3 Br Cl CH CH 3 CH 3 CH 2 CH H 2 C Br CH 2 CH 2 C CH CH HC CH CH Cl CH 2 CH CH 3 C CH CH CH CH CH CH 3 C CH 3 CH CH 2 CH 2 H 2 C CH 2 CH 2 Cl CH 2 CH 2 CH 3 Br CH 3 CH CH 2 CH 3 Br a) b) c) d) e) f) g) h) i) j) k) l) H 2 O PH 3 NH 3 N CH 3 CH 3 CH 3 : : OH - : .. .. O-CH 3 : .. .. - : : .. Na + I : - + + O-CH 3 H .. .. + + + + + + + Na + N 3 - : + Na + O-C O CH 3 : .. .. Na + O-C O CH 3 : .. .. + S-CH 3 H .. .. + I I
Background image of page 1

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

View Full DocumentRight Arrow Icon
1 (Con’t) Cl C(CH 3 ) 3 H H + SH .. .. S N 2 m) n) H Br CH 2 CH 3 CH 3 + I - acetone S N 2 H Br CH 2 CH 3 CH 3 o) + H 2 O S N 2 may 2. Write the mechanism of each reaction below. If a reaction involves two or more steps, indicate which step is slow. Use curved arrows !! CH 3 -O .. .. : + CH 3 -Br CH 3 O .. .. CH 3 + Br : A. B. CH 3 C Br CH 3 CH 3 + I : CH 3 C I CH 3 CH 3 + Br : Go to Next Page -------->
Background image of page 2
ANSWERS Assign 6-1 1. NOTE: Reactions m – o are S N 2 reactions. If you recall in class, I mentioned that in an S N
Background image of page 3

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

View Full DocumentRight Arrow Icon
Background image of page 4
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: 2 mechanism, the nucleophile bonds to the carbon from the side opposite the leaving group. This causes the configuration of the carbon to change (for example, in reaction n and o, from R to S. .. in reaction m , Cl leaving group is axial , but, the nucleophile bonds to the C from side opposite -Cl becoming equatorial ). C(CH 3 ) 3 H + S .. .. m) n) I o) HCl H CH 2 CH 3 CH 3 H OH CH 2 CH 3 CH 3 H Br-+ + HBr Go to Next Page -----> 2. CH 3-O .. .. : CH 3 CH 3 O .. .. CH 3 + Br : A. B. CH 3 C Br CH 3 CH 3 CH 3 C CH 3 CH 3 + Br : Br S N 2 slow S N 1 CH 3 C CH 3 CH 3 : I CH 3 C CH 3 CH 3 I fast...
View Full Document

Page1 / 4

Assign 6-1 - 2 mechanism, the nucleophile bonds to the...

This preview shows document pages 1 - 4. Sign up to view the full document.

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