Trouble generating files

I am trying to create 3 required files ca.pen, cert.pem and key.pem. I am receiving errors when inputing commands and following the docker guide.

Here is an except from the terminal:

Enter pass phrase for ca-key.pem:
Can't load /root/.rnd into RNG
140347370283456:error:2406F079:random number generator:RAND_load_file:Cannot open file:../crypto/rand/randfile.c:88:Filename=/root/.rnd
You are about to be asked to enter information that will be incorporated
into your certificate request.
What you are about to enter is what is called a Distinguished Name or a DN.
There are quite a few fields but you can leave some blank
For some fields there will be a default value,
If you enter '.', the field will be left blank.
-----
Country Name (2 letter code) [AU]:
State or Province Name (full name) [Some-State]:Queensland
Locality Name (eg, city) []:Brisbane
Organization Name (eg, company) [Internet Widgits Pty Ltd]:Docker Inc
Organizational Unit Name (eg, section) []:Sales
Common Name (e.g. server FQDN or YOUR name) []:206.189.187.199
Email Address []:Sven@home.org.au
root@docker-s-1vcpu-1gb-nyc1-01:~# openssl genrsa -out server-key.pem 4096
Generating RSA private key, 4096 bit long modulus (2 primes)
..........................................................................................................................................................................................................................................................................++++
.............................++++
e is 65537 (0x010001)

root@docker-s-1vcpu-1gb-nyc1-01:~# $ openssl req -subj "/CN=206.189.187.199" -sha256 -new -key server-key.pem -out server.csr
$: command not found
root@docker-s-1vcpu-1gb-nyc1-01:~# $ openssl req -subj "/CN=206.189.187.199" -sha256 -new -key server-key.pem -out server.csr
$: command not found
root@docker-s-1vcpu-1gb-nyc1-01:~# echo subjectAltName = DNS:206.189.187.199,IP:10.10.10.20,IP:127.0.0.1 >> extfile.cnf
root@docker-s-1vcpu-1gb-nyc1-01:~# echo extendedKeyUsage = serverAuth >> extfile.cnf

root@docker-s-1vcpu-1gb-nyc1-01:~# openssl x509 -req -days 365 -sha256 -in server.csr -CA ca.pem -CAkey ca-key.pem \
>   -CAcreateserial -out server-cert.pem -extfile extfile.cn
Can't open extfile.cn for reading, No such file or directory
139925498274240:error:02001002:system library:fopen:No such file or directory:../crypto/bio/bss_file.c:72:fopen('extfile.cn','r')
139925498274240:error:2006D080:BIO routines:BIO_new_file:no such file:../crypto/bio/bss_file.c:79:
root@docker-s-1vcpu-1gb-nyc1-01:~# openssl x509 -req -days 365 -sha256 -in server.csr -CA ca.pem -CAkey ca-key.pem \
>   -CAcreateserial -out server-cert.pem -extfile extfile.cnf
Can't open server.csr for reading, No such file or directory
140263526920640:error:02001002:system library:fopen:No such file or directory:../crypto/bio/bss_file.c:72:fopen('server.csr','r')
140263526920640:error:2006D080:BIO routines:BIO_new_file:no such file:../crypto/bio/bss_file.c:79:

root@docker-s-1vcpu-1gb-nyc1-01:~# 
root@docker-s-1vcpu-1gb-nyc1-01:~# openssl x509 -req -days 365 -sha256 -in server.csr -CA ca.pem -CAkey ca-key.pem \
>  -CAcreateserial -out server-cert.pem -extfile extfile.cnf
Can't open server.csr for reading, No such file or directory
139985191776704:error:02001002:system library:fopen:No such file or directory:../crypto/bio/bss_file.c:72:fopen('server.csr','r')
139985191776704:error:2006D080:BIO routines:BIO_new_file:no such file:../crypto/bio/bss_file.c:79:

Any assistance or advice would be most appreciated